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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.

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Official URL: http://dx.doi.org/10.1021/ol500768w


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
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

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