Jiong Lan

First total synthesis and absolute configuration of marine cembrane diterpenoid (+)-11,12-epoxysarcophytol A

A concise and efficient total synthesis of (+)-11,12-epoxysarcophytol A (1), an epoxy cembrane diterpenoid from marine soft coral Lobophytum, is described, which allows the assignment of an absolute configuration (11S,12S) of the epoxide function unambiguously.

An efficient total synthesis of (±)-sinulariol-B

Abstract The first total synthesis of (±)-Sinulariol-B, a marine cembrandiol, was achieved in ten steps and ∼10% overall yield from E-geraniol (8). The key steps were the coupling of sulfone 7 with allylic chloride 6 and the macrocyclization of precursor 5 by sulfone- and thioether-stabilized carbanionic alkylations, respectively.

Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol

Abstract An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (−)-4- O -(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol.

Enantioselective total synthesis of natural 11,12-epoxycembrene-C

Abstract The first enantioselective total synthesis of (+)-11,12-epoxycembrene-C (1), a novel naturally occurring cembranoxide isolated from tropical marine soft coral, was achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials.

The first total synthesis of (−)-sinulariol-B and three other cembranoids

Abstract The first total synthesis of (−)-sinulariol-B, a marine cembrandiol, was achieved from geraniol. Three other cembranoids were also synthesized from (−)-sinulariol-B.

The first total synthesis of preverecynarmin

Abstract Preverecynaimin, isolated from a pennatulatean coral, has been synthesized from E,E -farnesol.

Total Partial Synthesis of (3S, 6S)-(+)-3,7-Dimethyl-6-hydroxy-3-acetoxyocta-1,7-diene and (3S, 6S)-(–)-3,7-Dimethylocta-1,7-diene-3,6-diol from Geraniol

The synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7-diene and (3S, 6S)-(–)-3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.