Synthesis of the Pyranonaphthoquinones
Dehydroherbarin, (+)-Astropa­quinone B and (+)-Astropaquinone
C en Route to Ascomycones A and B

Andrew D. Wadsworth; Jonathan Sperry; Margaret A. Brimble

doi:10.1055/s-0029-1218832

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Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropaquinone B and (+)-Astropaquinone C en Route to Ascomycones A and B

Andrew D. Wadsworth, Jonathan Sperry, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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Abstract

The total syntheses of the pyranonaphthoquinone natural products dehydroherbarin, (+)-astropaquinone B and (+)-astropaquinone C are described. A late stage oxidation strategy employed for the synthesis of the astropaquinones was not amenable to the conversion of dehydroherbarin into the ascomycones. The syntheses of astropaquinones B and C reported herein constitute the first total syntheses and their absolute stereochemistry was determined to be (1R,3S).

Key words

pyranonaphthoquinone - ascomycone - astropaquinone - dehydroherbarin - thysanone - 3C-protease inhibitor

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References

<A NAME="RP05810SS-1">1</A> Singh SB. Cordingley MG. Ball RG. Smith JL. Dombrowski AW. Goetz MA. Tetrahedron Lett. 1991, 32: 5279

<A NAME="RP05810SS-2">2</A> Sperry J. Yuen TY. Brimble MA. Synthesis 2009, 2561

<A NAME="RP05810SS-3">3</A> Opatz T. Kolshorn H. Thines E. Anke H. J. Nat. Prod. 2008, 71: 1973 ; Ascomycones A and B were reported to show no detectable optical rotation and were thus assigned as racemic at C1

<A NAME="RP05810SS-4">4</A> Wang L. Dong JY. Song HC. Shen KZ. Wang LM. Sun R. Wang CR. Gao YX. Li GH. Li L. Zhang KQ. Planta Med. 2009, 75: 1339

<A NAME="RP05810SS-5A">5a</A> Kadkol MV. Gopalkrishnan KS. Narasimhachari N. J. Antibiot. 1971, 24: 245

<A NAME="RP05810SS-5B">5b</A> Nagarajan R. Narasimhachari N. Kadkol MV. Gopalkrishnan KS.
J. Antibiot. 1971, 24: 249

<A NAME="RP05810SS-6A">6a</A> Evans GE. Leeper FJ. Murphy JA. Staunton J.
J. Chem. Soc., Chem. Commun. 1979, 205

<A NAME="RP05810SS-6B">6b</A> Dodd JH. Weinreb SM. Tetrahedron Lett. 1979, 38: 3593

<A NAME="RP05810SS-7">7</A> Nakata H. Bull. Chem. Soc. Jpn. 1960, 33: 1693

<A NAME="RP05810SS-8">8</A> Zhang Z. Yu B. J. Org. Chem. 2003, 68: 6309

<A NAME="RP05810SS-9">9</A> Kesteleyn B. De Kimpe N. J. Org. Chem. 2000, 65: 640

<A NAME="RP05810SS-10">10</A> Xu YC. Lebeau E. Gillard JW. Attardo G. Tetrahedron Lett. 1993, 34: 3841

<A NAME="RP05810SS-11">11</A> Isobe K. Takeda N. Mohri K. Tsuda Y. Chem. Pharm. Bull. 1989, 12: 3390

<A NAME="RP05810SS-12">12</A> Harling JD. Orlek BS. Tetrahedron 1998, 54: 14905

<A NAME="RP05810SS-13">13</A> Chiarello J. Jouillé M. Tetrahedron 1988, 44: 41

<A NAME="RP05810SS-14A">14a</A> Gill M. Donner CD. Tetrahedron Lett. 1999, 40: 3921

<A NAME="RP05810SS-14B">14b</A> Donner CD. Gill M. J. Chem. Soc., Perkin Trans. 1 2002, 938

<A NAME="RP05810SS-15">15</A> Hansen CA. Frost JW. J. Am. Chem. Soc. 2002, 124: 5926

Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropa­quinone B and (+)-Astropaquinone C en Route to Ascomycones A and B

Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropaquinone B and (+)-Astropaquinone C en Route to Ascomycones A and B