title: Direct aldol strategy in enantioselective total synthesis of thuggacin B.
abstract: An enantioselective total synthesis of thuggacin B, a natural product exhibiting antibiotic activity against Mycobacterium tuberculosis, is described. Asymmetric direct aldol reactions promoted by Cu and Zn catalysts play a pivotal role in constructing four stereogenic centers. The use of direct aldol reactions as the initial steps for the synthesis of two key fragments allowed the construction of the other stereogenic centers through chirality transfer.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan), Fax: (+81) 3-3441-7589 http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index_e.html; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
authors.forename: Akinobu
authors.initials: A
authors.lastname: Matsuzawa
authors.forename: Christopher R
authors.initials: CR
authors.lastname: Opie
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000995:Antitubercular Agents; D018942:Macrolides; D013854:Thioamides; C523034:thuggacin B; D003300:Copper; C116609:3-hydroxybutanal; D015032:Zinc
keywords: direct aldol reactions; thioamides; thuggacins; total synthesis; tuberculosis