An Approach to a Bislactone Skeleton: A Scalable Total Synthesis of (+/-)-Penifulvin A

Das, Dipendu and Kant, Ruchir and Chakraborty, Tushar Kanti (2014) An Approach to a Bislactone Skeleton: A Scalable Total Synthesis of (+/-)-Penifulvin A. In: ORGANIC LETTERS, 16 (10). pp. 2618-2621.

PDF org_let_16-10_2618_2014.pdf - Published Version Restricted to Registered users only Download (1MB) | Request a copy

Abstract

An efficient and scalable total synthesis of the architecturally challenging sesquiterpenoid (+/-)-penifulvin A has been accomplished via a 12-step sequence with an overall yield of 16%. For the construction of this structurally complex tetracyclic molecule, the key steps used included 1,4-conjugate addition, a Pd(0) catalyzed cross-coupling reaction between an enol phosphate and trimethyl aluminum, Claisen rearrangement using the Johnson orthoester protocol, Ti(III)-mediated reductive epoxide opening-cyclization, Lewis acid catalyzed epoxy-aldehyde rearrangement, and finally a substrate controlled oxidative cascade lactonization process.

Item Type:	Journal Article
Publication:	ORGANIC LETTERS
Publisher:	AMER CHEMICAL SOC
Additional Information:	Copyright for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	24 Jun 2014 06:02
Last Modified:	24 Jun 2014 06:02
URI:	http://eprints.iisc.ac.in/id/eprint/49302

Actions (login required)

View Item