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A synthetic approach for constructing the 3/6/6/5-fused tetracyclic skeleton of tenuipesine A.

Authors :
Tian JM
Zhao X
Tu YQ
Gong W
Zhang FM
Zhang SY
Wang SH
Source :
Chemistry, an Asian journal [Chem Asian J] 2014 Mar; Vol. 9 (3), pp. 724-7. Date of Electronic Publication: 2014 Jan 16.
Publication Year :
2014

Abstract

An efficient approach toward the 3/6/6/5-fused tetracyclic skeleton of tenuipesine A has been accomplished. The strategy featured 1) a tandem Mitsunobu and 3,3-rearrangement reaction yielding the key intermediate 7 with two adjacent all-carbon quaternary centers with high d.r.; and 2) a tandem DBDMH-mediated semipinacol rearrangement via a 1,2-oxygen migration of an allylic hemiketal to construct the highly substituted tetrahydropyran ring.<br /> (Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1861-471X
Volume :
9
Issue :
3
Database :
MEDLINE
Journal :
Chemistry, an Asian journal
Publication Type :
Academic Journal
Accession number :
24436258
Full Text :
https://doi.org/10.1002/asia.201301581