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

DOI: 10.1248/cpb.41.1900

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1900 - 1905 (1993)

Update date:2022-08-04

Topics:

Authors:

Iwata Iwata

Murakami

Okuda Okuda

Morie Morie

Maezaki Maezaki

Yamashita

Kuroda Kuroda

Imanishi

Tanaka Tanaka

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Article abstract of DOI:10.1248/cpb.41.1900

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.

Full text of DOI:10.1248/cpb.41.1900

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