169895-74-3Relevant articles and documents
Stereocontrolled Total Synthesis of Hemibrevetoxin B
Kadota, Isao,Yamamoto, Yoshinori
, p. 6597 - 6606 (1998)
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 γ-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 γ-alkoxyallylstannane 30 from the corresponding allyl ether 29 in which the γ-alkoxy substituent became sterically quite bulky. This problem was solved by developing the acetal cleavage method for the synthesis of γ-alkoxyallylstannanes. The cyclization of 38 proceeded smoothly to give the key intermediate 5 in a highly stereoselective manner. Construction of the α-vinyl aldehyde and (Z)-diene moieties were performed using Nicolaou's protocol.
Total synthesis of hemibrevetoxin B
Kadota, Isao,Jung-Youl, Park,Koumura, Nagatoshi,Pollaud, Guy,Matsukawa, Yasuhisa,Yamamoto, Yoshinori
, p. 5777 - 5780 (2007/10/02)
The total synthesis of Hemibrevetoxin B is described. A new cyclization approach, based on the Lewis acid mediated intramolecular cyclization of the γ-oxo-substituted allylic tin having an aldehyde group, produced the 6-6-7-7 polycyclic ether skeleton of
