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Wang B, Xie Y, Yang Q, et al. Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation. Org Lett. 2016;18(20):5388-5391doi: 10.1021/acs.orglett.6b02767.
Wang, B., Xie, Y., Yang, Q., Zhang, G., & Gu, Z. (2016). Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation. Organic letters, 18(20), 5388-5391. https://doi.org/10.1021/acs.orglett.6b02767
Wang, Bin, et al. "Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation." Organic letters vol. 18,20 (2016): 5388-5391. doi: https://doi.org/10.1021/acs.orglett.6b02767
Wang B, Xie Y, Yang Q, Zhang G, Gu Z. Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation. Org Lett. 2016 Oct 21;18(20):5388-5391. doi: 10.1021/acs.orglett.6b02767. Epub 2016 Oct 05. PMID: 27701860.
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Org Lett. 2016 Oct 21;18(20):5388-5391. doi: 10.1021/acs.orglett.6b02767. Epub 2016 Oct 05.

Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation.

Organic letters

Bin Wang, Yuanzhen Xie, Qin Yang, Guozhu Zhang, Zhenhua Gu

Affiliations

  1. Department of Chemistry, University of Science and Technology of China , 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.
  2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.

PMID: 27701860 DOI: 10.1021/acs.orglett.6b02767

Abstract

A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]hexane from diazo compound with a bicyclo[2.2.1]heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki-Hiyama-Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde.

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