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Synthesis of Aristotelia‐ Type Alkaloids, Part XVI
Author(s) -
Galli Renato,
Dobler Markus,
Güller Rolf,
Stahl Reto,
Borschberg HansJürg
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3400::aid-hlca3400>3.0.co;2-2
Subject(s) - chemistry , oxidizing agent , reagent , natural product , indole alkaloid , alkaloid , absolute configuration , stereochemistry , total synthesis , organic chemistry
Two independent total syntheses of the Aristotelia alkaloid (−)‐serratenone ((−)‐ 1 ) are disclosed, one starting with (−)‐ α ‐pinene, the other one with ( S )‐ α ‐terpineol. These correlations led to a revision of the originally proposed absolute configuration of the natural product. In the course of systematic investigations of the behavior of the indole alkaloids (+)‐makomakine ((+)‐ 18 ) and (−)‐hobartine ((−)‐ 22 ) towards oxidizing reagents, it was found that treatment with I 2 leads to no less than five different products. Depending on the exact reaction conditions, each of them can be obtained as the major component in yields between 40 and 60%. One of these compounds was shown to be identical with the natural product (+)‐11,12‐didehydromakonin‐10‐one ((+)‐ 28 ).