Issue 2, 2016

Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A

Abstract

We report our synthetic studies towards the synthesis of the C3–C14 fragment of alchivemycin A. The synthesis featured an asymmetric alkylation with excellent diastereoselectivity and a one-pot Julia–Kocienski olefination with excellent E-selectivity. An intramolecular Diels–Alder reaction was employed to construct the highly functionalized cis-decalin framework. Interestingly, the stereochemical outcome was not expected to generate the two stereoisomers 20 and 21 instead of the desired cis-decalin 5. The detailed mechanism of this transformation was discussed. These synthetic endeavors have offered us a number of crucial insights for the synthesis of the complex natural product alchivemycin A.

Graphical abstract: Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A

Supplementary files

Article information

Article type
Research Article
Submitted
02 Xim 2015
Accepted
20 Kax 2015
First published
21 Kax 2015

Org. Chem. Front., 2016,3, 251-258

Author version available

Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A

K. Ma, D. Liao, S. Yang, X. Li and X. Lei, Org. Chem. Front., 2016, 3, 251 DOI: 10.1039/C5QO00343A

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