Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 71, No. 1, 2007, pp.75-85
Published online, 17th November, 2006
DOI: 10.3987/COM-06-10907
Total Synthesis of (4R,5S)-Melithiazol C and (3R,4S)-Cystothiazole E

Hiroyuki Takayama, Keisuke Kato, Masayuki Kimura, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

A Wittig reaction between (+)-chiral aldehyde (4R,5R)-3 and the phosphoranylide derived from the mono-thiazole-type phosphonium iodide [(±)-10] using lithium bis(trimethylsilyl)amide afforded the (+)-melithiazol C (1), whose spectral data were identical with those of the natural product [(+)-1]. Moreover, the Julia’s coupling of aldehyde (21) and the bithiazole-type sulfone (5) followed by the consecutive deprotection and Dess-Martin oxidation gave the (+)-cystothiazole E (2), whose spectral data were identical with those of the natural product [(+)-2].