✦ LIBER ✦

A stereocontrolled total synthesis of optically active (R,R)-phytol

✍ Scribed by Tamotsu Fujisawa; Toshio Sato; Tatsuo Kawara; Kazuo Ohashi

Book ID: 104243471
Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 239 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92354-8

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✦ Synopsis

A stereospecific synthesis of (R,R)-phytol with highZy stereochemical purity in both absolute and geometrical configurations was aehieved by utiZi,zing the 5~2 type ring-opening reaction of CR)-B-methyZ-fkpropiolactone, and the SLv2' type ring-opening reaction of isopropenyl oxirane, from CR)-pdegone as a starting material.

Phytol (1) occurs abundantly in plants as an alcohol part of the ester sidechain of chlorophyl, and is a useful material for the syntheses of a-tocopherol (vitamin E)' and phylloquinone (vitamin K1).2 Natural phytol is an acyclic diterpene alcohol possesing an R-configuration at two asymmetric carbons (CT and Cn) and an E-configuration of the double bond.3

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