Synthetic Studies on Aromadendrane-Type Compounds. I. Stereoselective Construction of Aromadendrane- and Alloaromadendrane-Type Skeletons

As a preliminary study for the synthesis of aromadendrane- and alloaromadendrane-type compounds, trans and cis B/C-ring compounds (18 and 22) were synthesized from (+)-(1S, 2R, 4R, 7R)-3, 3, 7-trimethyltricyclo[6.3.0.02, 4]undec-8-en-10-one (3) as a common intermediate, which was obtained from (+)-3...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1994/02/15, Vol.42(2), pp.300-305
Hauptverfasser:	TANAKA, Tetsuaki, FUNAKOSHI, Yousuke, UENAKA, Kenji, MAEDA, Kimiya, MIKAMIYAMA, Hidenori, TAKEMOTO, Yoshiji, MAEZAKI, Naoyoshi, IWATA, Chuzo
Format:	Artikel
Sprache:	eng
Schlagworte:	(+)-3-carene aldol condensation Alicyclic compounds, terpenoids, prostaglandins, steroids alloaromadendrane aromadendrane Chemistry Exact sciences and technology Organic chemistry Preparations and properties stereoselective reduction Terpenoids tricyclo[6.3.0.02, 4]undecane
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Zusammenfassung:	As a preliminary study for the synthesis of aromadendrane- and alloaromadendrane-type compounds, trans and cis B/C-ring compounds (18 and 22) were synthesized from (+)-(1S, 2R, 4R, 7R)-3, 3, 7-trimethyltricyclo[6.3.0.02, 4]undec-8-en-10-one (3) as a common intermediate, which was obtained from (+)-3-carene via an intramolecular aldol condensation as a crucial step.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.42.300