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Total Synthesis of (+)‐Batzelladine A and (−)‐Batzelladine D, and Identification of Their Target Protein
Author(s) -
Shimokawa Jun,
Ishiwata Takanori,
Shirai Koji,
Koshino Hiroyuki,
Tanatani Aya,
Nakata Tadashi,
Hashimoto Yuichi,
Nagasawa Kazuo
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500852
Subject(s) - guanidine , bicyclic molecule , chemistry , aldehyde , cycloaddition , alcohol , stereoselectivity , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
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.