Synthetic studies towards complex diterpenoids. Part 11. Stereochemically defined synthesis of the racemates of 1,2,3,4,4a,9a-hexahydro-7-methoxy-1-methylfluorene-1-carboxylic acid
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 804-808
- https://doi.org/10.1039/p19800000804
Abstract
Two simple synthetic routes to 1,2,3,4-tetrahydro-7-methoxy-1 -methylfluorene-1 -carboxylic acid (1b), a potential intermediate towards gibberellins, and its stereochemically defined transformations to three racemates of 1,2,3,4,4a,9a- hexahydro-7-methoxy-1 -methylfluorene-1 -carboxylic acid (4b)–(6b) are described. Catalytic hydrogenation of (1 b) yields a mixture of (5b) and (6b) in a ratio of ca. 95 : 5, whereas, lithium-liquid ammonia reduction of (1b) gives (4b) and (6b) in a ratio of ca. 23 : 77. A mechanism is proposed to explain the stereochemical results in the lithium–ammonia reduction of (1b) and related systems.Keywords
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