𝔖 Bobbio Scriptorium
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Synthesis of the Alleged Natural Monoterpenoid α-Santolinenone

✍ Scribed by Graizano Guella; Marino Cavazza; Antonio Guerriero; Francesco Pietra

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
375 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Authentic α‐santolinenone ( = (+)‐(4__R__)‐1(7)‐p‐menthen‐2‐one; (+)‐1) is made available for the the first time in 30% overall yield from (+)‐(4__R__)‐p‐menthene ((+)‐2) via the diastereoisomeric allylic alcohols (+)‐4a/(+)‐4b, which are oxidized to (+)‐1 with Ag~2~CO~3~/Celite. Yields are good, except for the last stage; indeed, only alcohol (+)‐4a, with equatorial OH‐group, undergoes oxidation, and (+)‐1 is partly substracted via a hetero Diels‐Alder dimerization giving a mixture of the diastereoisomeric dihydropyrans (+)‐5a/(+)‐5b. When Cr(VI) reagents ae used, (+)‐4a/(+)‐4b mainly give phellandral (6) and carvotanacetone (7), NnO~2~ reacts too sluggishly with (+)‐4a/(+)‐4b. A camphor pyrolyzate, previously thought to be 1 must be a different compound, probably 7.

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