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Diterpenoids of mixed biogenesis in phaeophyta biogenetic-type interconversions

1982; Elsevier BV; Volume: 38; Issue: 5 Linguagem: Inglês

10.1016/0040-4020(82)80215-9

1464-5416

Antonio González, Miguel Ángel Álvarez-Avitia, Julio D. Martı́n, Manuel Norte, Claudia Pérez‐Martínez, Juana Rovirosa,

Algal biology and biofuel production

In the course of research into marine natural products, the diterpenoids taondiol 10 and atomaric acid 15, were isolated from the brown seaweed Taonia atomaria. The similarities of these structures plus the fact that both compounds come from the same alga suggest that there may be a biogenetic relationship between the two. This speculated relationship is adumbrated in Scheme 1, where the cyclic and acyclic diterpenoids of mixed biogenesis isolated from Phaeophyta are interrelated. In the present work, the competitive cyclisation of the proposed olefinic intermediate 4 to the naturally occurring compounds taondiol 10, isotandiol 11, epitaondiol 12 and stypodiol 13, is reported. The stereoselective transformation of atomaric acid 15 into the compound 4 is also reported, which transformation occurs by intramolecular carbocylisation of the olefinic aldehyde 7 followed by backbone rearrangement to the olefin 4. This result prompted the proposal that atomaric acid 15 may arise in nature by means of a like rearrangement but operating in a reverse direction.