Terpenoid chemistry. XXV the absolute configuration of (-)-ngaione, (-)-epingaione and related substances

Russell C.A. and Sutherland M.D. (1982) Terpenoid chemistry. XXV the absolute configuration of (-)-ngaione, (-)-epingaione and related substances. Australian Journal of Chemistry, 35 9: 1881-1894. doi:10.1071/CH9821881


Author Russell C.A.
Sutherland M.D.
Title Terpenoid chemistry. XXV the absolute configuration of (-)-ngaione, (-)-epingaione and related substances
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 1445-0038
Publication date 1982-01-01
Sub-type Article (original research)
DOI 10.1071/CH9821881
Open Access Status Not yet assessed
Volume 35
Issue 9
Start page 1881
End page 1894
Total pages 14
Subject 1600 Chemistry
Abstract The absolute configuration of (-)-ngaione has been confirmed as (2’S,5’R)-4-methyl-l-(5’-methyl-2’,3’,4’,5’-tetrahydro[2’,3”-bifuran]-5’-yl)pentan-2-one as was proposed by Hegarty, Kelly, Park and Sutherland in 1970, by converting it into (-)-ngaiane, (2S,5S)-5-methyl-5-(4”-methylpentyl)-2,3,4,5-tetrahydro[2,3’-bifuran], which is shown to resist ring opening by nucleophiles. Further confirmation was obtained by the ozonolysis of (-)-ngaiane to (-)-(4R)-4,8-dimethylnonan-4-olide comparable in molecular rotation with (-)-(4S)-4-methylhexan-4-olide which has been correlated with (-)-(R)-linalooI. Wolff-Kishner reduction of the hydrazone or semicarbazone of (-)-ngaione yields mainly an E, Z mixture of (lS,4ζ)-l-(furan-3’-yl)-4,8-dimethylnon-5-en-l-ol with some ngaiane. Being (+)-ngaione, ipomeamarone does not have the absolute configuration assigned by Kubota, Nakajima and Matsuura in 1964. The name ipomeamarone is redundant, implies an incorrect stereochemistry and should be abandoned.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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