Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues

The stereoselective synthesis of two fragments (C1–C7 and C6–C22) of the anti‐tumor agent phostriecin has been achieved. The chiral hydroxy‐vinyl‐δ‐lactone building block (fragment C1–C7) was subsequently utilized for the synthesis of 5‐hydroxygoniothalamin, 5‐acetoxygoniothalamin, and their derivat...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-08, Vol.2018 (32), p.4389-4399
Main Authors: Purushotham Reddy, K., Vasudeva Reddy, D., Sabitha, Gowravaram
Format: Article
Language:English
Subjects:
Cross metathesis
Fragmentation
Fragments
Natural products
Stereoselectivity
Synthesis
Synthesis design
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Summary:The stereoselective synthesis of two fragments (C1–C7 and C6–C22) of the anti‐tumor agent phostriecin has been achieved. The chiral hydroxy‐vinyl‐δ‐lactone building block (fragment C1–C7) was subsequently utilized for the synthesis of 5‐hydroxygoniothalamin, 5‐acetoxygoniothalamin, and their derivatives. We have designed a convergent path for the synthesis of the key fragments (C1–C7 and C6–C22) of phostriecin. The approach not only provides ready access to several biologically active molecules, such as 5‐hydroxygoniothalamin, 5‐acetoxygoniothalamin, and their analogues, but also (S)‐5‐[(S)‐1‐hydroxyallyl]furan‐2(5H)‐one derivatives with cross metathesis as the key reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800561