Diterpenoids. XXXVII. Rearrangement of Methyl 13-Isopropyl-7-oxo-podocarpa-5,8,11,13-tetraen-15-oate by Means of Aluminum Chloride
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概要
- 論文の詳細を見る
The phenacylidene ester 2,methyl 13-isopropyl-7-oxo-podocarpa-5,8,11,13-tetraen-15-oate, underwent novel rearrangements on refluxing with an excess of aluminum chloride to afford 13-isopropyl-1α-methyl-1β-methoxycarbonyl-7-oxo-15,16-bisnor-10α-podocarpa-5,8,11,13-tetraene (7) and 10α-hydroxy-13-isopropyl-7-oxo-1,10-seco-spiro(1.5)-podocarpa-8,11,13-trien-15-oic acid 15→10 lactone (8) in 57 and 5% yields, respectively. Their structures were unequivocally established by chemical conversions and spectral examinations. The reaction courses (a) and (b) through 6 were proposed for the mechanisms of these rearrangements which somewhat differ from the rearrangement of 2 by means of protonic acid. It was further found that boron trifluoride etherate promoted also these rearrangement, but was less effective as catalyst, and treatment of 7 with aluminum chloride under the same condition led to the formation of 2 and 8 though in respective small yields.
- 公益社団法人日本薬学会の論文
- 1975-11-25
著者
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秋田 弘幸
Riken Institute (The Institute of Physical and Chemical Research)
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田原 昭
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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秋田 弘幸
Rikagaku Kenkyusho (The Institute of Physical and Chemical Research)
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田原 昭
Rikagaku Kenkyusho (the Institute Of Physical Chemical Research)
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