Radical Approach to the Chiral Quaternary Center in Asperaculin A: Synthesis of 9-Deoxyasperaculin A

Das, Dipendu ; Chakraborty, Tushar Kanti (2017) Radical Approach to the Chiral Quaternary Center in Asperaculin A: Synthesis of 9-Deoxyasperaculin A Organic Letters, 19 (3). pp. 682-685. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.6b03854

Related URL: http://dx.doi.org/10.1021/acs.orglett.6b03854

Abstract

Diastereoselective approaches toward the synthesis of a marine-derived sesquiterpenoid fungal metabolite, asperaculin A, are delineated, combining step economy and simplicity. Two distinct lactonization sequences from a common intermediate led to the first synthesis of 9-deoxyasperaculin A, a novel dioxa[5.5.5.6]fenestrane, in 14 steps (16% overall yield) and 16 steps (18% overall yield), respectively. [2,3]-Wittig–Still rearrangement and Ti(III)-mediated epoxide opening–cyclization were employed as some of the key steps for the stereoselective generation of the vicinal all-carbon quaternary centers of the target molecule.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:131091
Deposited On:02 Dec 2022 10:24
Last Modified:02 Dec 2022 10:24

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