Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.01, 6]dodecanes Corresponding to the B/C/D-Ring Systems

Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.01, 6]dodecanes Corresponding to the B/C/D-Ring Systems

Tricyclo[6.3.1.01.6]dodecane derivatives (5 and 6) corresponding to the B/C/D-ring systems of aphidicolane and stemodane diterpenes were synthesized stereoselectively via a spirodienone-alcohol (4) as a common intermediate. Participation of the neighboring hydroxyl group in 4 is crucial for controll...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1993/11/15, Vol.41(11), pp.1900-1905
Hauptverfasser: IWATA, Chuzo, MURAKAMI, Kazuo, OKUDA, Osamu, MORIE, Toshiya, MAEZAKI, Naoyoshi, YAMASHITA, Hiroshi, KURODA, Takeshi, IMANISHI, Takeshi, TANAKA, Tetsuaki
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
aphidicolane
Chemistry
Exact sciences and technology
hydroxyl group participation
Organic chemistry
Preparations and properties
regioselective reduction
spirodienone
stemodane
tricyclo[6.3.1.01, 6]dodecane
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Zusammenfassung:Tricyclo[6.3.1.01.6]dodecane derivatives (5 and 6) corresponding to the B/C/D-ring systems of aphidicolane and stemodane diterpenes were synthesized stereoselectively via a spirodienone-alcohol (4) as a common intermediate. Participation of the neighboring hydroxyl group in 4 is crucial for controlling the stereochemistry of the spirocenters.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.41.1900