An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones

Jennifer I. Aird; A. N. Hulme; John W. White

doi:10.1021/ol062932z

An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones

Jennifer I. Aird, A. N. Hulme, John W. White

Research output: Contribution to journal › Article › peer-review

Abstract / Description of output

A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehydes with unsaturated beta-hydroxy ketones, and conditions for the RCM cyclization of the resultant dienes have been optimized to give high yields of medium ring lactones. The synthetic utility of this sequence is demonstrated through generation of the fully functionalized core of octalactin A.

Original language	English
Pages (from-to)	631-634
Number of pages	4
Journal	Organic letters
Volume	9
DOIs	https://doi.org/10.1021/ol062932z
Publication status	Published - 2007

Keywords / Materials (for Non-textual outputs)

Evans-Tishchenko
medium ring lactone
octalactin A

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10.1021/ol062932z

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title = "An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones",

abstract = "A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehydes with unsaturated beta-hydroxy ketones, and conditions for the RCM cyclization of the resultant dienes have been optimized to give high yields of medium ring lactones. The synthetic utility of this sequence is demonstrated through generation of the fully functionalized core of octalactin A.",

keywords = "Evans-Tishchenko, medium ring lactone, octalactin A",

author = "Aird, {Jennifer I.} and Hulme, {A. N.} and White, {John W.}",

year = "2007",

doi = "10.1021/ol062932z",

language = "English",

volume = "9",

pages = "631--634",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones

AU - Aird, Jennifer I.

AU - Hulme, A. N.

AU - White, John W.

PY - 2007

Y1 - 2007

N2 - A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehydes with unsaturated beta-hydroxy ketones, and conditions for the RCM cyclization of the resultant dienes have been optimized to give high yields of medium ring lactones. The synthetic utility of this sequence is demonstrated through generation of the fully functionalized core of octalactin A.

AB - A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehydes with unsaturated beta-hydroxy ketones, and conditions for the RCM cyclization of the resultant dienes have been optimized to give high yields of medium ring lactones. The synthetic utility of this sequence is demonstrated through generation of the fully functionalized core of octalactin A.

KW - Evans-Tishchenko

KW - medium ring lactone

KW - octalactin A

U2 - 10.1021/ol062932z

DO - 10.1021/ol062932z

M3 - Article

SN - 1523-7060

VL - 9

SP - 631

EP - 634

JO - Organic letters

JF - Organic letters

ER -

An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones

Abstract / Description of output

Keywords / Materials (for Non-textual outputs)

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