Watanabe Kazuhiro, Iwasaki Katsuhiko, Abe Toshiaki, Inoue Munenori, Ohkubo Kôichi, Suzuki Takeyuki, Katoh Tadashi
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
Org Lett. 2005 Aug 18;7(17):3745-8. doi: 10.1021/ol051398c.
A convergent route to (-)-candelalide A involved the union of a trans-decalin portion (AB ring) and a gamma-pyrone moiety through the C16-C3' bond to assemble the whole carbon framework and subsequent formation of the dihydropyran ring (C ring) as the crucial steps. A strategic [2,3]-Wittig rearrangement was employed for establishing the stereogenic center at C9 and an exo-methylene function at C8 present in the decalin portion. [reaction: see text]
一条合成（-）-坎德拉利德A的汇聚路线涉及通过C16-C3'键将反式十氢化萘部分（AB环）和γ-吡喃酮部分结合起来，以构建整个碳骨架，随后形成二氢吡喃环（C环）作为关键步骤。采用了一种策略性的[2,3]-维蒂希重排来在十氢化萘部分中C9处建立手性中心以及在C8处建立亚甲基外取代基。[反应：见正文]
