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Synthesis 2016; 48(11): 1630-1636
DOI: 10.1055/s-0035-1561592
DOI: 10.1055/s-0035-1561592
special topic
Asymmetric Total Syntheses of the trans-2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and E from a Common Precursor
Further Information
Publication History
Received: 12 January 2016
Accepted after revision: 02 March 2016
Publication Date:
12 April 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201611/lookinside/thumbnails/ss-2016-c0023-st_10-1055_s-0035-1561592-1.jpg)
Abstract
Asymmetric total syntheses of diospongin B and parvistones D and E are reported. Our strategy features a high-yielding three-step reaction sequence: Achmatowicz rearrangement, reductive γ-deoxygenation, and Matsuda–Heck coupling to construct the rare and challenging trans-2-aryl-6-alkyltetrahydropyrans, which serve as common intermediates for the syntheses of diospongin B, and parvistones D and E.
Key words
diospongin B - parvistone E - trans-tetrahydropyran - Achmatowicz rearrangement - 9-deoxygoniopypyrone - 8-epi-9-deoxygoniopypyroneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561592.
- Supporting Information
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For recent reviews on THP synthesis, see:
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For a review, see:
For recent total synthesis of leiocarpin A, see: