In vitro studies of tetracyclic diterpenoid biosynthesis

✍ Scribed by J.W. Blunt; E.J. Ditzel; M.P. Hartshorn; Lu Hieng Sieng; M.H.G. Munro; W.T. Robinson

• Book ID: 104241674
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 135 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90479-4

✦ Synopsis

The structure of a novel pentacyclic diterpene ether (7) is presented.

In the boron trifluoride diethyletherate catalysed rearrangement of the 7,&epoxyisopimar-15-ene skeleton (la-c) a pentacyclic ether is formed. 1,2 The structure and mode of formation of the ether was of considerable interest as the 15-ene was involved and potentially represented a demonstration of the involvement of the vinyl group in the type of cyclisation required by the postulated route for tetracyclic diterpenoid biosynthesis.3 Isolation of an aldehyde with the rearranged skeleton (2c-d) 2,4,5 however,precluded that possibility since (2~) on further reaction gave the pentacyclic ether (7~).