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- Title
Desymmetrisation of meso‐2,4‐Dimethyl‐8‐oxabicyclo[3.2.1]‐oct‐6‐ene‐3‐ol and its Application in Natural Product Syntheses.
- Authors
Tadiparthi, Krishnaji; Anand, Pragya; Sakirolla, Raghavendra; Gupta, T. Prakash; Jadhav, Krishna A; Kishore Das, Sukant; Singh Yadav, Jhillu
- Abstract
The compounds containing chiral centers and different functional groups serve as magnificent building blocks for the preparation of various natural products that are having immense biological activity. "Dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol" is one of the wonderful synthons to construct multiple stereo centers at a time during the asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various simple and complex natural products from the past three decades (1995–2020) by using dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol as a synthon. Moreover, the synthetic utility of this starting material was investigated and well demonstrated. Further, we executed the desymmetrization of dimethyl‐8‐oxa‐bicyclo[3.2.1]oct‐6‐en‐3‐ol by hydroboration to get different chiral centers. After obtaining the stereocenters, we could manage either the fragment, formal or total synthesis of natural products, by simple protection and deprotection sequence followed by C−C bond formation steps.
- Subjects
NATURAL products; CHIRAL centers; HYDROBORATION; FUNCTIONAL groups; ASYMMETRIC synthesis
- Publication
Chemical Record, 2022, Vol 22, Issue 3, p1
- ISSN
1527-8999
- Publication type
Article
- DOI
10.1002/tcr.202100286