A Short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide

Vasamsetty, L and Khan, Faiz Ahmed and Mehta, G (2015) A Short, general, Suzuki–Miyaura coupling anchored approach to 3-alkenylbutenolides: total synthesis of akolactones A & B, hamabiwalactone B and ancepsenolide. Tetrahedron, 71 (21). pp. 3209-3215. ISSN 0040-4020

Full text not available from this repository. (Request a copy)

Abstract

An efficient and versatile synthesis of 3-alkenylbutenolides through direct Suzuki–Miyaura cross coupling reaction between preformed 3-halobutenolides and a range of readily accessible boronic acids has been devised. The coupling process exhibits good functional group compatibility and is preparatively viable. The methodology has been applied to achieve short syntheses of natural products rac-akolactones A & B and rac-hamabiwalactone B. The scope of the Suzuki–Miyaura reaction based protocol has been further amplified through the synthesis of 3,3′-alkenyl-bis-butenolides by employing α, ω-bis-boronic acids as coupling partners and applied to a synthesis of bioactive natural product rac-ancepsenolide.

[error in script]

IITH Creators:

IITH Creators	ORCiD
Khan, Faiz Ahmed	UNSPECIFIED

Item Type:

Article

Additional Information:

L.V. and F.A.K. wish to thank the Council of Scientific and Industrial Research in India for the award of a Research Fellowship and research support, respectively. G.M. acknowledges the research support from Eli Lilly and Jubilant-Bhartia Foundations and the facilities extended by the University of Hyderabad.

Uncontrolled Keywords:

Butenolides; Alkenylbutenolides; Boronic acid synthesis; Suzuki–Miyaura coupling; Natural products synthesis

Subjects:

Chemistry > Analytical chemistry

Divisions:

Department of Chemistry

Depositing User:

Team Library

Date Deposited:

11 Aug 2015 06:35

Last Modified:

21 Sep 2017 06:27