Diterpenoid total synthesis, an A .far. B .far. C approach. VII. Total synthesis of DL-sugiol, DL-ferruginol, and DL-nimbiol

Facile Total Synthesis of (±)‐Nimbiol

“…8 Meyer synthesized (±)-nimbiol through a A®AB®ABC strategy by 14 steps in low yield. 9 As an extension of our previous work, 10,11 herein we report an efficient total synthesis of (±)-nimbiol. The salient feature of our approach lies in that the A/B ring was all trans fusion.…”

Practical and Efficient Strategy for Synthesis of Ferruginol, Sugiol, and Sugiol Methyl Ether from Geraniol

“…Thus, the unique and simple structure of aromatic abietane diterpenoids can be used as a template for lead compounds in the development of new drugs that are derived from natural products. Although several methods have been developed for the synthesis of 1 , 2 , and 3 from, e.g., podocarpic acid, dehydroabietic acid, clareol, dehydroabietylamine, 2,2,6‐trimethylcyclohexanone/sodium p ‐methoxyphenylacetylide, and α ‐cyclocitral, some have disadvantages including multiple steps, tedious separation, and expensive starting materials. Herein, we report a practical and efficient strategy for the synthesis of 1 , 2 , and 3 from a simple starting material: geraniol (Scheme ).…”

A Synthetic View on Momilactones and Related 9β-H Pimarane Skeleton Diterpenoids

“…The stereoselective synthesis of (±)-4,4-dinor-9 β -H-pimara-7,15-diene ( 42 ) was accomplished by Sicherer-Roetman Sicherer-Roetman et al (1985) . Initially Meyer ( Meyer et al 1975 ) formed the trans-syn-cis tricyclic product 50 with formyl enone 34 and tert-butyl 3-oxopentanoate 49 ( Scheme 2A ). Formylation and dehydrogenation of decalone 47 provided the starting compound 34 .…”