Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin

Airan, Yougant and Prasad, Kavirayani R (2019) Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin. In: JOURNAL OF ORGANIC CHEMISTRY, 84 (22). pp. 14974-14979.

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Abstract

Synthesis of the 14-membered macrolide core of migrastatin is accomplished by the use of fury' carbinol in 13 linear steps from furfural with similar to 11% overall yield. Key strategies in the synthesis include the oxidative ring opening of furan and its use as a four-carbon synthon, S(N)2 displacement of a functionalized ally' bromide, and ring closing metathesis to obtain the macrolactone.

Item Type:	Journal Article
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
Additional Information:	copy right of this article belong to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	11 Dec 2019 09:55
Last Modified:	11 Dec 2019 09:55
URI:	http://eprints.iisc.ac.in/id/eprint/64053

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