Stereoselective Total Synthesis of (–)‐Batzellasides A, B, and C. Issue 14 (19th March 2013)

• Record Type: Journal Article
• Authors: Okaki, Toru; Fujimura, Ryohei; Sekiguchi, Masataka; Zhou, Dejun; Sugimoto, Kenji; Minato, Daishiro; Matsuya, Yuji; Kato, Atsushi; Adachi, Isao; Tezuka, Yasuhiro; Saporito, Ralph A.; Toyooka, Naoki
• Is Part Of: European journal of organic chemistry. Issue 14(2013)
• Page Start: 2841
• Page End: 2848
• Publication Date: 2013-03-19
• Subjects: Natural products -- Total synthesis -- Asymmetric synthesis -- Allylation -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201567
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Total synthesis of (–)‐L ‐batzellasides A, B, and C has been achieved in 13 steps from known lactone2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain. Abstract : Total synthesis of (–)‐batzellasides A, B, and C has been achieved in 13 steps from known lactone2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1 position by acyliminium chemistry and Brown's asymmetric allylation of the corresponding aldehydes to construct a stereocenter on the side chain.