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Molecules 2016, 21(9), 1197; doi:10.3390/molecules21091197

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

1
Dipartimento di Chimica, Università degli Studi di Roma “La Sapienza”, P.le Aldo Moro, 5, I-00185 Roma, Italy
2
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)

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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