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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3420 - 3425

DOI: https://doi.org/10.6023/cjoc202005058

Asymmetric Total Synthesis of the Possible Structure 1b of 15-Oxopuupehenoic Acid

  • Song Huayue ,
  • Liu Lin ,
  • Xie Xingang
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  • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Received date: 2020-05-22

  Revised date: 2020-05-29

  Online published: 2020-06-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21472079).

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Abstract

15-Oxopuupehenoic acid is a new merosesquiterpenoid isolated in 2009 by Crews group from the crude sponge extracts prioritized a Papua New Guinea collection of Hyrtios sp. Its possible structure was deduced to be tetracyclic chromanones 1a~1b or benzo[c]oxepin-1(3H)-ones 1c~1d based on the spectra data, and later determinded to be 1a by analysis of its gHMBC correlations spectra. Recently Alvarez-Manzaneda and Chahboun group obtained 1a by chemical synthesis which spectra data did not match well with those of natural 15-oxopuupehenoic acid. We started from R-(-)-carvone and approched its possible structure 1b through a convergent coupling-cyclization strategy. Our sythesis featured Suzuki carbonylative coupling reaction and KOH promoted intramolecular cyclization reaction to construct the unique chromanone subunit. The spectra data of synthetic 1b did not match well with those of natural 15-oxopuupehenoic acid either which indicated its structure needed revision.

Key words： 15-oxopuupehenoic acid; Suzuki carbonylative coupling; KOH promotion; intramolecular cyclization; chromanone

Cite this article

Song Huayue , Liu Lin , Xie Xingang . Asymmetric Total Synthesis of the Possible Structure 1b of 15-Oxopuupehenoic Acid[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3420 -3425 . DOI: 10.6023/cjoc202005058

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