127681-58-7Relevant articles and documents
SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE NATURAL COMPOUNDS. PART I: STEREOSPECIFIC TRANSFORMATION OF UVIDIN A INTO (-)-CINNAMODIAL
Garlaschelli, L.,Vidari, G.
, p. 7371 - 7378 (1989)
A partial synthesis of (-)-cinnamodial (1) has been achived, using (+)-uvidin A (3) as starting material.This also represents a formal synthesis of (-)-cinnamosmolide (2a) and pereniporin B (2b).
Synthesis of (-)-albrassitriol and (-)-6-epi-albrassitriol from (+)-larixol
Vlad, Pavel F.,Ciocarlan, Alexandru,Coltsa, Mihai,Edu, Carolina,Biriiac, Andrei,Barba, Alic,Deleanu, Calin,Nicolescu, Alina,Dambrosio, Michele,De Groot, Aede
, p. 809 - 817 (2013/06/05)
A novel synthesis of natural drimanic compounds, (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), has been carried out starting from an easily available labdane diterpenoid, (+)-larixol (1). In a two-step procedure, (+)-larixol (1) was converted into 14,15-bisnorlab-7-ene-6,13-dione (9), which was then submitted to a Norrish type II photochemical degradation yielding drim-7,9(11)-diene-6-one (10), whose treatment with OsO4 led selectively to the formation of drim-7-ene-9α,11-diol-6-one (12). The same compound was obtained by selective epoxidation of the C(9)-C(11) double bond in drim-7,9(11)-diene-6-one (10) with monoperphtalic acid. Treatment of the resulting mixture of α-and β-epoxides (13 and 14) with HClO 4 yielded drim-7-ene-9α,11-diol-6-one (12). Reduction of the C6-carbonyl group in drim-7-ene-9α,11-diol-6-one (12) with LiAlH 4 afforded (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), 12.4% and 13.6% overall yields, respectively.