The Tricyclo[9.3.1.03,8]pentadecane System— A Short Synthesis of a C-Aromatic Taxane Skeleton

✍ Scribed by Prof. Dr. Kenneth J. Shea; Dr. Peter D. Davis

• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: English
• Weight: 235 KB
• Volume: 22
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198304191

✦ Synopsis

ture and oxygen over a long period of time[4a1. It was also obtained by reaction of 4 with elemental sulfur (60% yield). Reaction of 2 with chlorine affords 2,4,6-tri-tert-butylphenyfphosphonic dichloride almost quantitatively after hydrolysis'za1.

The yields of compounds 2, 3[4b1, and 4 (20-60%, 1-8%, and 1-40%, respectively) depend on the ratio 1 : Mg.

3 had already been synthesized via an alternative route by Cetinkaya et al., who also carried out a crystal structure analysis.

The molecule 2 contains a two-fold crystallographic axis, which bisects the P-S-P angle (Fig. ). The atoms P, C l , P', and C1' form a plane (deviation 0.02 A); the interplanar angle between a benzene ring and the plane P, C1, P', C1' is 59.3". The benzene rings are distorted to a boat form, in which the largest distortion (14.4") is a little smaller than in bis(2,4,6-tri-tert-butylphenyl)phosphinic chloride (18.5 0)[2b1.