Synlett 2018; 29(15): 1933-1936
DOI: 10.1055/s-0037-1610149
synpacts
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Astellatol: A Three-Decade Synthetic Puzzle

Nan Zhao
Department of Chemistry, and Shenzhen Grubbs Institute, Southern University of Science and Technology, No. 1088 Xueyuan Ave. Nanshan, Shenzhen, Guangdong, 518055, P. R. of China   Email: xuj@sustc.edu.cn
,
Shengling Xie
Department of Chemistry, and Shenzhen Grubbs Institute, Southern University of Science and Technology, No. 1088 Xueyuan Ave. Nanshan, Shenzhen, Guangdong, 518055, P. R. of China   Email: xuj@sustc.edu.cn
,
Hengjun Huang
Department of Chemistry, and Shenzhen Grubbs Institute, Southern University of Science and Technology, No. 1088 Xueyuan Ave. Nanshan, Shenzhen, Guangdong, 518055, P. R. of China   Email: xuj@sustc.edu.cn
,
Jing Xu  *
Department of Chemistry, and Shenzhen Grubbs Institute, Southern University of Science and Technology, No. 1088 Xueyuan Ave. Nanshan, Shenzhen, Guangdong, 518055, P. R. of China   Email: xuj@sustc.edu.cn
› Author Affiliations
Financial support from NSFC (21402082, 21772082), SZDRC Discipline Construction Program, and SZSTI (JCYJ20170817110515599, KQJSCX20170728154233200) is gratefully acknowledged.
Further Information

Publication History

Received: 03 April 2018

Accepted after revision: 17 April 2018

Publication Date:
28 May 2018 (online)

Abstract

Here we briefly discuss and review our journey to achieve the first, enantiospecific total synthesis of a rare, complex sesterterpenoid, astellatol.

1 Introduction

2 Model Study of Reductive Radical Cyclization

3 Total Synthesis of Astellatol

4 Conclusion

 
  • References

    • 1a Liu Y. Wang L. Jung JH. Zhang S. Nat. Prod. Rep. 2007; 24: 1401
    • 1b Wang L. Yang B. Lin XP. Zhou XF. Liu Y. Nat. Prod. Rep. 2013; 30: 455 ; and references therein
    • 2a Sadler IH. Simpson TJ. J. Chem. Soc., Chem. Commun. 1989; 1602
    • 2b Sadler IH. Simpson TJ. Magn. Reson. Chem. 1992; 30: 18
  • 3 Hog DT. Mayer P. Trauner D. J. Org. Chem. 2012; 77: 5838
  • 4 Kawahara N. Nozawa M. Flores D. Bonilla P. Sekita S. Satake M. Kawai K. Chem. Pharm. Bull. 1997; 45: 1717
  • 5 Kaneda M. Takahashi R. Iitaka Y. Shibata S. Tetrahedron Lett. 1972; 4609
  • 6 Hensens OD. Zink D. Williamson JM. Lotti VJ. Chang RS. L. Goetz MA. J. Org. Chem. 1991; 56: 3399
  • 7 Corey EJ. Desai MC. Engler TA. J. Am. Chem. Soc. 1985; 107: 4339
    • 8a Paquette LA. Wright J. Drtina GJ. Roberts RA. J. Org. Chem. 1987; 52: 2960
    • 8b Wright J. Drtina GJ. Roberts RA. Paquette LA. J. Am. Chem. Soc. 1988; 110: 5806
    • 9a Hudlicky T. Radesca-Kwart L. Li LQ. Bryant T. Tetrahedron Lett. 1988; 29: 3283
    • 9b Hudlicky T. Fleming A. Radesca L. J. Am. Chem. Soc. 1989; 111: 6691
  • 10 Wender PA. Singh SK. Tetrahedron Lett. 1990; 31: 2517
  • 11 Hog DT. Webster R. Trauner D. Nat. Prod. Rep. 2012; 29: 752
    • 12a Hog DT. Huber FM. E. Mayer P. Trauner D. Angew. Chem. Int. Ed. 2014; 53: 8513
    • 12b Hog DT. Huber FM. E. Jiménez-Osés G. Mayer P. Houk KN. Trauner D. Chem. Eur. J. 2015; 21: 13646
    • 13a Zhao N. Xie S. Chen G. Xu J. Chem. Eur. J. 2016; 22: 12634
    • 13b Zhao N. Yin S. Xie S. Yan H. Ren P. Chen G. Chen F. Xu J. Angew. Chem. Int. Ed. 2018; 57: 3386
    • 14a Weinges K. Schmidbauer SB. Schick H. Chem. Ber. 1994; 127: 1305
    • 14b Johnston D. McCusker CM. Procter DJ. Tetrahedron Lett. 1999; 40: 4913
    • 14c Johnston D. McCusker CM. Muir K. Procter DJ. J. Chem. Soc., Perkin Trans. 1 2000; 681
    • 14d Johnston D. Francon N. Edmonds DJ. Procter DJ. Org. Lett. 2001; 3: 2001
    • 14e Johnston D. Couché E. Edmonds DJ. Muir KW. Procter DJ. Org. Biomol. Chem. 2003; 1: 328
    • 14f Hutton TK. Muir KW. Procter DJ. Org. Lett. 2003; 5: 4811
    • 14g Edmonds DJ. Muir KW. Procter DJ. J. Org. Chem. 2003; 68: 3190
    • 14h Harb HY. Collins KD. Altur JV. G. Bowker S. Campbell L. Procter DJ. Org. Lett. 2010; 12: 5446
    • 14i Harb HY. Procter DJ. Synlett 2012; 6
    • 14j Takema K. Masaatsu A. Toshio N. Chem. Lett. 2012; 41: 287
    • 14k Nocquet P.-A. Hazelard D. Gruntz G. Compain P. J. Org. Chem. 2013; 78: 6751
    • 14l Chuang H.-Y. Isobe M. Org. Lett. 2014; 16: 4166
    • 14m Chen J.-P. He W. Yang Z.-Y. Yao Z.-J. Org. Lett. 2015; 17: 3379
    • 14n Chuang H.-Y. Isobe M. J. Org. Chem. 2017; 82: 2045
    • 14o Chuang H.-Y. Isobe M. Tetrahedron 2017; 73: 2705
  • 15 Marx JN. Norman LR. J. Org. Chem. 1975; 40: 1602
    • 16a Tang Y. Deng L. Zhang Y. Dong G. Chen J. Yang Z. Org. Lett. 2005; 7: 593
    • 16b Tang Y. Zhang Y. Dai M. Luo T. Deng L. Chen J. Yang Z. Org. Lett. 2005; 7: 885
    • 16c Tang YF. Deng LJ. Zhang YD. Dong GB. Chen JH. Yang Z. Org. Lett. 2005; 7: 1657
    • 16d Lan Y. Deng LJ. Liu J. Wang C. Wiest O. Yang Z. Wu YD. J. Org. Chem. 2009; 74: 5049
    • 16e Xiao Q. Ren W. Chen Z. Sun T. Li Y. Ye Q. Gong J. Meng F. You L. Liu Y. Zhao M. Xu L. Shan Z. Shi Y. Tang Y. Chen J. Yang Z. Angew. Chem. Int. Ed. 2011; 50: 7373
    • 16f Sun T. Ren W. Xiao Q. Tang Y. Zhang Y. Li Y. Meng F. Liu Y. Zhao M. Xu L. Chen J. Yang Z. Chem. Asian J. 2012; 7: 2321
    • 16g Li Y. Chen Z. Xiao Q. Ye Q. Sun T. Meng F. Ren W. You L. Xu L. Wang Y. Chen J. Yang Z. Chem. Asian J. 2012; 7: 2334
    • 16h Ren W. Chen Z. Xiao Q. Li Y. Sun T. Zhang Z. Ye Q. Meng F. You L. Zhao M. Xu L. Tang Y. Chen J. Yang Z. Chem. Asian J. 2012; 7: 2341
    • 16i Liu Q. Yue G. Wu N. Lin G. Li Y. Quan J. Li C. Wang G. Yang Z. Angew. Chem. Int. Ed. 2012; 51: 12072
    • 16j Wang Y. Xu L. Yu R. Chen J. Yang Z. Chem. Commun. 2012; 8183
    • 16k Huang J. Fang L. Long R. Shi L. Shen H. Li C. Yang Z. Org. Lett. 2013; 15: 4018
    • 16l Shi L. Shen H. Fang L. Huang J. Li C. Yang Z. Chem. Commun. 2013; 8806
    • 16m Liu S. Shen H. Yu Z. Shi L. Yang Z. Lan Y. Organometallics 2014; 33: 6282
    • 16n You L. Liang X. Xu L. Wang Y. Zhang J. Su Q. Li Y. Zhang B. Yang S. Chen J. Yang Z. J. Am. Chem. Soc. 2015; 137: 10120
    • 16o Zhang J. Wang X. Li S. Li D. Liu S. Lan Y. Gong J. Yang Z. Chem. Eur. J. 2015; 21: 12596
    • 16p Huang J. Fang L. Gong J. Li C. Yang Z. Tetrahedron 2015; 71: 3720
    • 16q Shi L. Yang Z. Eur. J. Org. Chem. 2016; 2356
    • 16r Lv C. Yan X. Tu Q. Di Y. Yuan C. Fang X. Ben-David Y. Xia L. Gong J. Shen Y. Yang Z. Hao X. Angew. Chem. Int. Ed. 2016; 55: 7539
    • 16s Liu D. Sun T. Wang K. Lu Y. Zhang S. Li Y. Jiang Y. Chen J. Yang Z. J. Am. Chem. Soc. 2017; 139: 5732
    • 16t Lv C. Tu Q. Gong J. Hao X. Yang Z. Tetrahedron 2017; 73: 3612
  • 17 Hung K. Condakes ML. Morikawa T. Maimone TJ. J. Am. Chem. Soc. 2016; 138: 16616
  • 18 Hayashi Y. Koshino S. Ojima K. Kwon E. Angew. Chem. Int. Ed. 2017; 56: 11812
    • 19a Corey EJ. Engler TA. Tetrahedron Lett. 1984; 25: 149
    • 19b Hutchins RO. Natale NR. J. Org. Chem. 1978; 43: 2299
    • 19c Mandai T. Matsumoto T. Kawada M. Tsuji J. J. Org. Chem. 1992; 57: 1326