NDLI: Total Synthesis of Bryostatin 16 via Atom Economical and Chemoselective Approaches

Content Provider	PubMed Central
Author	Trost, Barry M. Dong, Guangbin
Abstract	Atom economy1 and chemoselectivity2 constitute two of the major challenges for enhancement of synthetic efficiency. The syntheses of complex natural products constitute the most demanding arena for exploration of such principles. The combination of extraordinary promising biological activity and the structural complexity of the bryostatins with the benchmark provided by earlier syntheses of some members make them an excellent target for such studies. Herein, we report a concise total synthesis of bryostatin 16 (1). Bryostatin 16 was chosen as the specific synthetic target, most critically because bryostatin 16 could potentially act as a pivotal parent structure to allow access to almost all other bryostatins. Moreover, its synthesis could provide an essential chemical probe by enabling facile analogue syntheses with variations in most parts of the structure, to allow fine-tuning of the biological functions. Application of atom economical and chemoselective reactions under development in these laboratories provides ready access to polyhydropyrans, common structural features of numerous polyacetate-polypropionate derived natural products. Most notably, our strategy of employing the combination of two transition metal catalysts (palladium and gold) demonstrates a new chemoselective and atom-economical macrocyclization reaction between two different alkynes and subsequent formation of the C-ring dihydropyran in the context of a complex natural product synthesis.
Related Links	http://dx.doi.org/10.1038/nature07543
Ending Page	488
Page Count	4
Starting Page	485
File Format	PDF
ISSN	00280836
e-ISSN	14764687
Journal	Nature
Issue Number	7221
Volume Number	456
Language	English
Publisher Date	2008-11-27
Access Restriction	Open
Subject Keyword	General Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Multidisciplinary

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
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