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Ren W.-W.,Peking University | Ren W.-W.,Peking University of Shenzhen Graduate School | Chen Z.-X.,Peking University | Chen Z.-X.,Peking University of Shenzhen Graduate School | And 23 more authors.
Chemistry - An Asian Journal | Year: 2012

The final phase for the total synthesis of (±)-schindilactone A (1) is described herein. Two independent synthetic approaches were developed that featured Pd-thiourea-catalyzed cascade carbonylative annulation reactions to construct intermediate 3 and a RCM reaction to make intermediate 4. Other important steps that enabled the completion of the synthesis included: 1) A Ag-mediated ring-expansion reaction to form vinyl bromide 17 from dibromocyclopropane 30; 2) a Pd-catalyzed coupling reaction of vinyl bromide 17 with a copper enolate to synthesize ketoester 16; 3) a RCM reaction to generate oxabicyclononenol 10 from diene 11; 4) a cyclopentenone fragment in substrate 8 was constructed through a Co-thiourea-catalyzed Pauson-Khand reaction (PKR); 5) a Dieckmann-type condensation to successfully form the A ring of schindilactone A (1). The chemistry developed for the total synthesis of schindilactone A (1) will shed light on the synthesis of other family members of schindilactone A. Three to get ready, now... The completion of the total synthesis of (±)-schindilactone A is reported. The chemistry developed for the total synthesis of schindilactone A will shed light on the synthesis of other family members of schindilactone A. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Li Y.,Peking University | Li Y.,Peking University of Shenzhen Graduate School | Chen Z.-X.,Peking University | Chen Z.-X.,Peking University of Shenzhen Graduate School | And 20 more authors.
Chemistry - An Asian Journal | Year: 2012

The successful synthesis of the highly complex model compound (2) of the CEFGH ring system of schindilactone A (1) is described. Several synthetic methodologies were developed and applied to achieve this goal, including ring-closing metathesis (RCM) and Co-thiourea-catalyzed Pauson-Khand reactions. Furthermore, two independent approaches were developed for the construction of the GH ring of model compound 2, the key steps of which included Pd-thiourea-catalyzed carbonylative annulation, methylation, and sequential RCM/oxa-Michael-addition reactions. The chemistry developed herein has provided a greater understanding of the synthesis of schindilactone A (1) and its analogous compounds of the same family. Two for the show: A highly complex model compound of the CEFGH ring system of schindilactone A (1) was synthesized. Key steps included Pd-thiourea-catalyzed carbonylative annulation, methylation, and sequential RCM/oxa-Michael-addition reactions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Wang Z.,Tsinghua University | Wang Z.,Peking University of Shenzhen Graduate School | Zhao K.,Tsinghua University | Fu J.,Peking University of Shenzhen Graduate School | And 4 more authors.
Organic and Biomolecular Chemistry | Year: 2013

The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved. © The Royal Society of Chemistry 2013.

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