Huaiji Zheng

Pt-Catalyzed Tandem 1,2-Acyloxy Migration/Intramolecular [3 + 2] Cycloaddition of Enynyl Esters

A platinum-catalyzed tandem reaction involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach to five-, six-, or seven-membered cyclic polyfunctional compounds.

Efficient asymmetric total syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate.

Concise and efficient asymmetric total syntheses of three substituted alpha-pyrone-type natural products have been accomplished via 7-9 steps from 5b in high overall yields, which involve linchpin coupling, ring-closing metathesis, and a tandem sequence of deacetylation and intramolecular oxa-Michael addition as the key steps.

Tandem Oxidative Dearomatization/Intramolecular Diels–Alder Reaction for Construction of the Tricyclic Core of Palhinine A

A concise construction of the 6/6/5 tricyclic core of Lycopodium alkaloid palhinine A (1) has been accomplished. The developed synthetic strategy featured a tandem oxidative dearomatization/intramolecular Diels-Alder reaction to construct C/D rings and an intramolecular 5-exo-trig radical cyclization to install the B ring of palhinine A (1). The developed approach paves the way for the total synthesis of palhinine A (1).

Asymmetric Total Synthesis of Cladosporin and Isocladosporin

The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthesis.

Total synthesis of (-)-Przewalskin B.

The first total synthesis of (-)-Przewalskin B has been accomplished with an intramolecular nucleophilic acyl substitution (INAS) reaction and an intramolecular aldol condensation as key steps.

Biomimetic total synthesis of (+)-chabranol.

A concise, biomimetic total synthesis of the unprecedented terpenoid skeleton (+)-chabraol has been accomplished via 6 steps from the chiral epoxide 7, involving an intramolecular Prins double cyclization to yield the bicyclo[2.2.1] core of the natural product as the key step. The absolute configuration of natural chabranol was also designated through the first asymmetric total synthesis.

Stereoselective Synthesis of Fused Spiroindolines via Tandem Mannich/Intramolecular Aminal Formation

A novel tandem Mannich/intramolecular aminal formation between tryptamines and salicylaldehydes was reported. This strategy provides a promising approach for the stereoselective synthesis of a range of complex fused spiroindolines, which bear a highly congested contiguous spiro quaternary center and two tertiary stereocenters, in a highly economical and effective fashion.

Studies on the Synthesis of Bitungolides A-E : Synthesis of the C(1)-C(12) Fragment

Synthesis of the core segment of bitungolides A-E has been achieved in 17 steps and 4.7% overall yield. Six stereogenic centers of bitungolides A-E were established via allylation, dihydroxylation, Myers alkylation, and Evans aldol reaction.