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Introduction of oxygen function into isoprenoid systems by means of Botrytis cinerea (Persoon)
Author(s) -
DmochowskaGladysz J.,
Kolek T.,
Siewiński A.,
Derdziński K.,
Zabża A.,
Nespiak A.
Publication year - 1986
Publication title -
journal of basic microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.58
H-Index - 54
eISSN - 1521-4028
pISSN - 0233-111X
DOI - 10.1002/jobm.3620261003
Subject(s) - hydroxylation , botrytis cinerea , double bond , chemistry , stereochemistry , oxygen , side chain , bond cleavage , ketone , diterpene , terpenoid , organic chemistry , botany , biology , catalysis , enzyme , polymer
The introduction of oxygen functions into (±)‐ 1 ‐( 2′,2′,3′ ‐trimethyl‐ 3′ ‐cyclopenten‐1′ ‐yl)‐propan‐2‐one [(±)‐ 1a ], (±)‐ 1‐ ( 2′,2′,3′ ,‐trimethyl‐3′‐cyclopenten‐1′ ‐yl)‐butan‐2‐one [(±)‐ 1b ], and (±)‐ 1 ‐ (2′, 3′, 3′‐trimethyl‐3′ ‐cyclopenten‐1′ ‐yl)‐pentan‐2‐one [(±)‐1c)] by Botrytis cinerea was carried out by hydroxylation in α position with respect to the double bond, or by epoxidation of the double bond itself. The main products had the hydroxy group at the methyl on the double bond. Simultaneously, a hydroxylation at the C′‐5 position in 1a and 1b was observed. In 1e , an additional hydroxylation occurred at the C‐4 position of the side chain. All the reactions were enantiospecific.