Synlett 2015; 26(07): 927-930
DOI: 10.1055/s-0034-1380122
letter
© Georg Thieme Verlag Stuttgart · New York

Biomimetic Total Synthesis of 6a,7,8,9,10,10a-Hexahydro-3,6,9-trimethyl-6-(4-methylpent-3-en-1-yl)-1,9-epoxy-6H-dibenzo-[b,d]pyran and Its Diastereoisomer

Huiying Zeng*
The Key Laboratory of Coordination Chemistry of Jiangxi, Province and College of Chemistry and Chemical Engineering, Jinggangshan University, Ji’an, Jiangxi 343009, P. R. of China   Email: zenghuiying2005@163.com
,
Daiping Duan
The Key Laboratory of Coordination Chemistry of Jiangxi, Province and College of Chemistry and Chemical Engineering, Jinggangshan University, Ji’an, Jiangxi 343009, P. R. of China   Email: zenghuiying2005@163.com
,
Boxiao Tang
The Key Laboratory of Coordination Chemistry of Jiangxi, Province and College of Chemistry and Chemical Engineering, Jinggangshan University, Ji’an, Jiangxi 343009, P. R. of China   Email: zenghuiying2005@163.com
› Author Affiliations
Further Information

Publication History

Received: 30 November 2014

Accepted after revision: 27 December 2014

Publication Date:
10 February 2015 (online)


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Abstract

The first total synthesis of 6a,7,8,9,10,10a-hexahydro-3,6,9-trimethyl-6-(4-methylpent-3-en-1-yl)-1,9-epoxy-6H-dibenzo[b,d]pyran and its diastereoisomer via tandem pericyclic reactions were achieved in one step. Our biomimetic strategy features a sequential Aldol-type addition, 6π electrocyclization, and hetero-Diels–Alder cycloaddition, where three rings, two C–C bonds, and two C–O bonds were spontaneously constructed in a highly efficient way.

Supporting Information