Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels–Alder/Claisen rearrangement

EJ Tisdale, I Slobodov, EA Theodorakis

文献索引：Tisdale, Eric J.; Slobodov, Irina; Theodorakis, Emmanuel A. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 24 p. 4418 - 4422

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被引用次数: 56

摘要

A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels–Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels–Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group ...