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

Chuzo IWATA; Kazuo MURAKAMI; Osamu OKUDA; Toshiya MORIE; Naoyoshi MAEZAKI; Hiroshi YAMASHITA; Takeshi KURODA; Takeshi IMANISHI; Tetsuaki TANAKA

doi:10.1248/cpb.41.1900

Synthetic Studies on Aphidicolane and Stemodane Diterpenes. II. Neighboring Hydroxyl Group Participation in Stereoselective Syntheses of Tricyclo[6.3.1.0^{1, 6}]dodecanes Corresponding to the B/C/D-Ring Systems

Chuzo IWATA, Kazuo MURAKAMI, Osamu OKUDA, Toshiya MORIE, Naoyoshi MAEZAKI, Hiroshi YAMASHITA, Takeshi KURODA, Takeshi IMANISHI, Tetsuaki TANAKA

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Keywords: tricyclo[6.3.1.0^{1, 6}]dodecane, aphidicolane, stemodane, hydroxyl group participation, spirodienone, regioselective reduction

JOURNAL FREE ACCESS

1993 Volume 41 Issue 11 Pages 1900-1905

DOI https://doi.org/10.1248/cpb.41.1900

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Abstract

Tricyclo[6.3.1.0^1.6]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.

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