A Biomimetic Synthesis of Phaitanthrin E Involving a Fragmentation of sp3 Carbon鈥揅arbon Bond: Synthesis and Rearrangement of Phaitanthrin D to Phaitanthrin E
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- 作者：Sagar D. Vaidya ; Narshinha P. Argade
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：December 18, 2015
- 年：2015
- 卷：17
- 期：24
- 页码：6218-6221
- 全文大小：350K
- ISSN：1523-7052
文摘
A biogenetic type total synthesis of alkaloids phaitanthrin D and phaitanthrin E has been described. The Csp3鈥揅sp3 bond cleavage with the release of several heteroatoms bearing unexpected leaving groups in intramolecular substitution reactions on an iminium double bond in the quinazolinones has been demonstrated using HMDS/ZnCl2 or NaHMDS. The mechanistic aspects have been supported by isolation and characterization of appropriate intermediates.