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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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
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Language:English
Subjects:
Allylation
Asymmetric synthesis
Natural products
Nitrogen heterocycles
Total synthesis
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cited_by cdi_FETCH-LOGICAL-c3557-5c6c53707d41f52b44fe14833bc7eb77873cfe1045b4f9e55df12ab865ca2cbe3
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container_issue 14
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container_title European journal of organic chemistry
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creator 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
description 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.
doi_str_mv 10.1002/ejoc.201201567
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subjects Allylation
Asymmetric synthesis
Natural products
Nitrogen heterocycles
Total synthesis
title Stereoselective Total Synthesis of (-)-Batzellasides A, B, and C
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