Rapid Construction of the [6-6-6-5] Tetracyclic Skeleton of the Daphniphyllum Alkaloid Daphenylline

You can call me Al: A concise route for construction of the [6‐6‐6‐5] tetracyclic skeleton of daphenylline, a structurally novel Daphniphyllum alkaloid, has been developed with full stereocontrol in only 8 steps from two known fragments. This approach features an intramolecular [3+2] cycloaddition o...

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Published inChemistry, an Asian journal Vol. 7; no. 11; pp. 2519 - 2522
Main Authors Li, Huilin, Zheng, Jiyue, Xu, Shiyan, Ma, Donghui, Zhao, Changgui, Fang, Bowen, Xie, Xingang, She, Xuegong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.11.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
alkaloids
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkenes - chemistry
Chemistry
cycloaddition
Cycloaddition Reaction
daphenylline
Embryophyta - chemistry
natural products
synthesis
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Summary:You can call me Al: A concise route for construction of the [6‐6‐6‐5] tetracyclic skeleton of daphenylline, a structurally novel Daphniphyllum alkaloid, has been developed with full stereocontrol in only 8 steps from two known fragments. This approach features an intramolecular [3+2] cycloaddition of a 2‐azaallyl anion with an alkene to form the cis‐fused AC rings.
Bibliography:ArticleID:ASIA201200625
istex:70138B9B304B5D973D8966E84875C72290BC7B49
MOST - No. 2010CB833200
NSFC - No. 21125207; No. 21072086; No. 21102062
ark:/67375/WNG-XRBP21ZM-M
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201200625