DITERPENOID TOTAL SYNTHESIS .16. ALTERNATIVE SYNTHETIC ROUTES TO (+-+)-STEVIOL AND (+1-)-KAUR-16-EN-19-OIC ACID
DITERPENOID TOTAL SYNTHESIS .16. ALTERNATIVE SYNTHETIC ROUTES TO (+-+)-STEVIOL AND (+1-)-KAUR-16-EN-19-OIC ACID
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DOI：
10.1080/00021369.1971.10859997
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发表时间：
1971-01-01
期刊：
影响因子：
--
通讯作者：
MATSUI, M
中科院分区：
文献类型：
--
作者：
NAKAHARA, Y;MORI, K;MATSUI, M
Diterpenoid Total Synthesis. Part XVI 919 were announced.", 121 In our own total synthesis of (•})-steviol, 11) we employed a novel skeletal rearrangement reaction" as the key-step. However, in order to ascertain the stereochemistry of the rearrangement products, we felt it necessary to prepare the desired stereoisomer(XXX) by a well-established authentic method.At the time of our work two methods were available for the construction of the C/D ring system. One was the cyclization of acetylenic ketones developed by Stork et al."' while the other was elaborated by Ireland et al. in the course of their total synthesis of (•})-hibaene. 15,'s. We decided to adopt the second method which was expected to be methodologically reliable as an authentic way. Our efforts along this line led to the alternative total syntheses of (•})-steviol(IIa) and(•})-kaur-16-en-19-oic acid (III). The latter also exhibits
