Zuosheng Liu

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.

HIGHLY STEREOSELECTIVE SYNTHESIS OF NERYLGERANIOL-18-OIC ACID

A stereoselectively total synthesis of nerylgeraniol-18-oic acid from geraniol was described. The key steps were the iodization- rearrangement of 2, 3-epoxy alcohol 4, stereoselective Claisen rearrangement and Horner-Emmons olefination reaction.

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.

Enantioselective total synthesis of (+)-3,4-epoxycembrene-A

Abstract A concise and efficient total synthesis of (+)-3,4-epoxycembrene-A 1 , an epoxy cembrane diterpenoid from tropical marine soft coral, is described. The synthesis features the use of an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps.

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.

First enantioselective total synthesis of (−)-13-hydroxyneocembrene

The first enantioselective total synthesis of (−)-13-hydroxyneocembrene (1), a naturally occurring cembranoids isolated from soft coral Sarcophyton trocheliophorum, was achieved via a general approach by employing intramolecular McMurry coupling as a key step from (S)-(+)-carvone.

First enantioselective total synthesis of (natural) (+)-11,12-epoxy-11,12-dihydrocembrene-C and (−)-7,8-epoxy-7,8-dihydrocembrene-C

The first enantioselective total syntheses of (+)-11,12-epoxy-11,12-dihydrocembrene-C 1 and (−)-7,8-epoxy-7,8-dihydrocembrene-C 2, two naturally occurring cembranoxides isolated from tropical marine soft corals, are achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials. The syntheses presented here verify the absolute stereochemistry assignment of 1 as (11S,12S) by Bowden et al. two decades ago, and the epoxy configuration of 2 was assumed as (7R,8R) accordingly.

The first total synthesis of preverecynarmin

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