1998年9月
Stereocontrolled total synthesis of hemibrevetoxin B
JOURNAL OF ORGANIC CHEMISTRY
- ,
- 巻
- 63
- 号
- 19
- 開始ページ
- 6597
- 終了ページ
- 6606
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo9807619
- 出版者・発行元
- AMER CHEMICAL SOC
The stereocontrolled total synthesis of hemibrevetoxin B (1) has been achieved in 56 steps and 0.75% overall yield from D-mannose. The intramolecular reaction of gamma-alkoxyallylstannane with. aldehyde is a key step for the present total synthesis. Thus, the BF3. OEt2-mediated reaction of 24 gave 6 as a sole product. We encountered difficulty in the synthesis of gamma-alkoxyallylstannane 30 from the corresponding allyl ether 29 in which the gamma-alkoxy substituent became sterically quite bulky. This problem was solved by developing the acetal cleavage method for the synthesis of gamma-alkoxyallylstannanes. The cyclization of 38 proceeded smoothly to give the key intermediate 5 in a highly stereoselective manner. Construction of the alpha-vinyl aldehyde and (Z)-diene moieties were performed using Nicolaou's protocol.
- リンク情報
- ID情報
-
- DOI : 10.1021/jo9807619
- ISSN : 0022-3263
- CiNii Articles ID : 80010557977
- Web of Science ID : WOS:000076233400036