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Molecules 2016, 21(9), 1197;

(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †

Dipartimento di Chimica, Università degli Studi di Roma “La Sapienza”, P.le Aldo Moro, 5, I-00185 Roma, Italy
Dipartimento di Biologia Ambientale, Università degli Studi di Roma “La Sapienza”, P.le Aldo Moro, 5, I-00185 Roma, Italy
Dedicated to Professor Karel Wiesner, our unforgotten mentor, on the thirtieth anniversary of his death.[...]
Author to whom correspondence should be addressed.
Academic Editors: Carlo Siciliano and Constantinos M. Athanassopoulos
Received: 6 August 2016 / Revised: 1 September 2016 / Accepted: 2 September 2016 / Published: 8 September 2016
(This article belongs to the Special Issue Synthesis of Bioactive Compounds from the Chiral Pool)
Full-Text   |   PDF [5451 KB, uploaded 8 September 2016]   |  


In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned. View Full-Text
Keywords: aphidicolin; stemodin; stemarin; podocarpic acid; synthesis aphidicolin; stemodin; stemarin; podocarpic acid; synthesis

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La Bella, A.; Leonelli, F.; Migneco, L.M.; Marini Bettolo, R. (+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †. Molecules 2016, 21, 1197.

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