Tunable Cyclization Strategy for the Synthesis of
Zizaene-, allo-Cedrane-, seco-Kaurane-,
and seco-Atesane-Type Skeletons

Lee, Chi-Sing

Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

Posted on 2017-09-20 - 22:14

A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.

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Yang, Qianqian; Ma, Wenjing; Wang, Gaopeng; Bao, Wenli; Dong, Xiaoshu; Liang, Xuefeng; et al. (2017). Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02610

https://doi.org/10.1021/acs.orglett.7b02610

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