A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)coronafacic acid and a formal synthesis of (+)-coriolin

Mehta, Goverdhan and Reddy, Srinivasa D (2001) A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)coronafacic acid and a formal synthesis of (+)-coriolin. In: Journal of Chemical Society: Perkin Transactions 1 (10). pp. 1153-1161.

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Abstract

A ready access to enantiopure 3,10-dioxygenated tricyclo$[5.2.1.0^2^,^6]$decane derivatives is reported. An effcient enzymatic kinetic resolution is employed through transesterification in the presence of lipase PS immobilized on Celite. Absolute configuration of the tricyclo$[5.2.1.0^2^,^6]$decan-10-one derivatives has been secured through correlation with (1R,2S)-1-aminoindan-2-ol. The promising utility of these enantiopure tricyclo$[5.2.1.0^2^,^6]$decane derivatives in synthesis has been demonstrated through the preparation of several optically pure cis-hydrindanes 15 18, employing the Haller-Bauer reaction as the key step for unbridging the trinorbornyl system. The cis-hydrindane (-)16 has been further elaborated to the natural product (+)-coronafacic acid (+)-24. In an interesting sequence, cis-hydrindanone(+)-18 has been transformed into cis-hydroisoquinolones (+)-30 and (+)-33 via photorearrangement of the derived oxaziridines 29 and 32, respectively. The hydroisoquinolones (+)-30 and (+)-33 can serve as useful enantiopure building blocks for the synthesis of complex indole alkaloids. Oxidative cleavage of the trinorbornene double bond in the tricyclo$[5.2.1.0^2^,^6]$decan-10-one derivative (-)-37 and functional-group adjustments leads to the optically pure diquinane (+)-38, an advanced intermediate in the total synthesis of (+)-coriolin (+)-34.

Item Type:	Journal Article
Publication:	Journal of Chemical Society: Perkin Transactions 1
Publisher:	The Royal Society of Chemistry
Additional Information:	Copyright for this article belongs to The Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	02 Feb 2005
Last Modified:	19 Sep 2010 04:17
URI:	http://eprints.iisc.ac.in/id/eprint/2687

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