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DOI: 10.1039/A708795K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1423-1426

Facile access to optically active ring C aromatic diterpene derivatives from manool. Highly efficient syntheses of (+)-12-methyl-7-oxo-podocarpa-8,11,13-triene-13-carboxylic acid, (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid and (+)-nimbiol

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Tatsuhiko Nakano, Randolph Alonso, María Aracelis Maillo, Alfonso Martín and Ramona Avila Núñez

Abstract

The extension of our recently developed strategy using the key intermediate 2, obtainable in two steps (52% overall yield) from manool 1, to the synthesis of naturally occurring ring C aromatic diterpene derivatives provides in three steps (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid 4b and its isomer 6b, and in seven steps (+)-nimbiol 11b, in good overall yields. This synthesis discloses that the structure 4b assigned to margolone isolated from Azadirachta indica A. Juss is incorrect and needs to be reinvestigated.

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