Stereoselective Total Synthesis of (-)-Batzellasides A, B, and C

Total synthesis of (–)‐L‐batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 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&...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-05, Vol.2013 (14), p.2841-2848
Main 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
Format: Article
Language:English
Subjects:
Allylation
Asymmetric synthesis
Natural products
Nitrogen heterocycles
Total synthesis
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Summary:Total synthesis of (–)‐L‐batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 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. Total synthesis of (–)‐batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201567