A vicinal diol approach for the total synthesis of molestin E ent-sinulacembranolide A and ent-sinumaximol A
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...
| Main Authors: | , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2022
|
| Summary: | 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. |
|---|