Journal article
A vicinal diol approach for the total synthesis of molestin E ent-sinulacembranolide A and ent-sinumaximol A
- Abstract:
- In this work an approach for the synthesis of furanocembranoid natural products containing the C-7,8-diol moiety is disclosed. This culminated in the first total synthesis of the natural product molestin E, together with ent-sinulacembranolide A and entsinumaximol A as well as a thorough exploration of their chemistry. Late-stage ring-closure of the C-7,8-diols to the corresponding epoxides was also demonstrated. Key features of this synthetic strategy include a stereoselective Baylis-Hillman reaction, ringclosing metathesis and Shiina macrolactonisation. Chiral-pool materials were deployed to ensure the desired absolute stereochemistry which was confirmed by late-stage single crystal Xray diffraction.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 5.5MB, Terms of use)
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- Publisher copy:
- 10.1002/chem.202202464
Authors
- Publisher:
- Wiley
- Journal:
- Chemistry - A European Journal More from this journal
- Volume:
- 28
- Issue:
- 63
- Article number:
- e202202464
- Publication date:
- 2022-09-06
- Acceptance date:
- 2022-08-09
- DOI:
- EISSN:
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1521-3765
- ISSN:
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0947-6539
- Language:
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English
- Keywords:
- Pubs id:
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1273379
- Local pid:
-
pubs:1273379
- Deposit date:
-
2022-08-10
Terms of use
- Copyright holder:
- Hoff et al
- Copyright date:
- 2022
- Rights statement:
- © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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