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Synthetic Studies on Dolabellane Diterpenoids. Synthesis of 10-epi-Clavudiol A, an Epimer of a Marine Dolabellanoid
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- Kato Nobuo
- Institute of Advanced Material Study Kyushu University
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- Nakanishi Kohji
- Institute of Advanced Material Study Kyushu University
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- Omoto Mineko
- Institute of Advanced Material Study Kyushu University
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- Mori Akira
- Institute of Advanced Material Study Kyushu University
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- Takeshita Hitoshi
- Tohwa Institute for Orient Studies Tohwa University
Bibliographic Information
- Other Title
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- Synthetic Studies on Dolabellane Diterp
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Description
In the line of our synthetic studies on the medium-ring containing higher terpenoids, we have applied our strategy, which is featured by obtaining a diterpenic skeleton from two monoterpene units, to the synthesis of the dolabellane family having a fused 5-11 bicyclic skeleton. From functionalized iridoid and geranyl synthons, 10-epi-clavudiol A, an epimer of marine dolabellane clavudiol A, has been totally synthesized. Noteworthy steps include a feasible isomerization of the more substituted double bond to the less substituted one via the reduction of the allylic chloride mediated by Cr(II)Cl_2 in the presence of alcoholic proton source and an intramolecular pinacol coupling to form the eleven-membered ring.
Journal
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- 九州大学機能物質科学研究所報告
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九州大学機能物質科学研究所報告 12 (1), 37-44, 1998-07-31
Institute of Advanced Material Study Kyushu University
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Details 詳細情報について
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- CRID
- 1390853649765665152
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- NII Article ID
- 110006177543
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- NII Book ID
- AN10060378
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- ISSN
- 09143793
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- DOI
- 10.15017/7892
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- HANDLE
- 2324/7892
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- NDL BIB ID
- 4544951
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- Text Lang
- en
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- Article Type
- departmental bulletin paper
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- Data Source
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- JaLC
- IRDB
- NDL Search
- CiNii Articles
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- Abstract License Flag
- Allowed