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Total synthesis of dl-hop ether, an iridoid monoterpene

✍ Scribed by Takeshi Imagawa; Nobuyiki Murai; Tetsuo Akiyama; Mituyosi Kawanisi

Book ID: 104244740
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 128 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93625-1

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✦ Synopsis

An iridoid monoterpene hop ether, 2,2-dimethyl-6-methylene-3-oxabicyclo[3.3.O]octane, was first synthesized in six steps starting from the protected lactol form of 3-formyl-2-methoxycarbonylcyclopentanol. Hop ether (I_) was isolated from Japanese hop. 2) It occupies a unique position in the iridoid monoterpenes since it is the most straightforward one, in a biogenetical sense, from the geraniol precursor and it has no functional group on both of isopropyl methyl groups of the iridane skeleton.3) We wish here to report the first synthesis of dl-hop ether (1). Recently we reported4) that anodic oxidation of the anion of 1. via oxygen-assisted Wagner-Meerwein rearrangement afforded the protected from (2) of 2-substituted 3-formylcyclopentanol.

The synthetic sequence starts with this compound (A).

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