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Studies for a Diastereoselective Synthesis of the Tetracyclic Diterpenic Diol Stemarin: A Model Study for a New Preparation of the Key Intermediate and the Synthesis of (+)-18-Deoxystemarin

✍ Scribed by Marco Berettoni; Rinaldo Marini Bettolo; Vittorio Montanari; Teresa Prencipe; Sergio Romeo


Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
585 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis


In the course of the cited synthesis of (*)-la, compound 3a was in fact obtained as a major epimer, along with 3b. The synthesis of (&)-la was then carried on with the minor epimer 3b [4].


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## Abstract (3__S__,4__R__)‐8‐Nonene‐3,4‐diol (2), the key intermediate for the synthesis of the bark beetle pheromone (+)‐__endo__‐brevicomin (1), has been synthesized in 46% overall yield (10 steps) based on erythritol (6) by employing lipase‐mediated asymmetric acetylation as one of the steps.