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Total Synthesis of (+)-Batzelladine A and (−)-Batzelladine D, and Identification of Their Target Protein

✍ Scribed by Jun Shimokawa; Takanori Ishiwata; Koji Shirai; Hiroyuki Koshino; Aya Tanatani; Tadashi Nakata; Yuichi Hashimoto; Kazuo Nagasawa

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
229 KB
Volume
11
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

Asymmetric total synthesis of batzelladine A (1) and batzelladine D (2) has been achieved. Our synthesis of batzelladines features 1) stereoselective construction of the cyclic guanidine system by means of successive 1,3‐dipolar cycloaddition reaction and subsequent cyclization, 2) direct esterification of the bicyclic carboxylic acid 35 with the guanidine alcohol 8 or 59 to construct the whole carbon skeleton of batzelladines, and 3) one‐step formation of the α,β‐unsaturated aldehyde 53 from the primary alcohol 47 with tetra‐n‐propylammoniumperruthenate (TPAP), providing an efficient route to the left‐hand bicyclic guanidine alcohol of batzelladine A (1). With the synthetic compounds 1 and 2 in hand, their target protein was examined by using immobilized CD4 and gp120 affinity gels. The results indicated that batzelladines A (1) and D (2) bind specifically to CD4.

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Total Synthesis of (+)-Batzelladine A an
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

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Scheme 1. Synthetic strategy toward batzelladines A and D. Boc = tertbutoxycarbonyl, Cbz = carbobenzyloxy, MPM = 4-methoxyphenylmethyl, TBS = tert-butyldimethylsilyl.