Stereoselective Total Synthesis of Paecilomycins E and F

Nisith Bhunia; Biswanath Das

doi:10.1055/s-0034-1380400

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(10): 1499-1509
DOI: 10.1055/s-0034-1380400

paper

Stereoselective Total Synthesis of Paecilomycins E and F

Nisith Bhunia

Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India eMail: biswanathdas@yahoo.com

,

Biswanath Das*

Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India eMail: biswanathdas@yahoo.com

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Abstract

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This paper is dedicated to Oishika (the daughter of the senior author, B. Das) on the occasion of her 20^th birthday.

Abstract

The stereoselective total synthesis of two bioactive resorcylic acid lactones, paecilomycins E and F has been accomplished thorough a general pathway using cis-butene-1,4-diol as the starting material. The pivotal steps of the synthesis include Sharpless asymmetric epoxidation, Bestmann–Ohira alkynation, Jacobsen kinetic resolution, and Heck coupling reaction.

Key words

resorcylic acid lactones - paecilomycin E - paecilomycin F - total synthesis - cis-butene-1,4-diol

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