Synthesis of the Southern FGHI Ring System of Azaspiracid-1 and Investigation into the Controlling Elements of C28- and C36-Ketalization

Heading south: An efficient approach to the FGHI southern ring system of azaspiracid‐1 is disclosed. Each of the eight stereogenic centers is generated with excellent diastereoselectivity. In addition, the stereochemical outcome of the ketalization steps could be controlled by careful selection of t...

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Published inAngewandte Chemie (International ed.) Vol. 45; no. 45; pp. 7622 - 7626
Main Authors Zhou, Xiao-Ti, Lu, Liang, Furkert, Daniel P., Wells, Charles E., Carter, Rich G.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.11.2006
WILEY‐VCH Verlag
Wiley
Subjects
aldol reaction
azaspiracids
Chemistry
Chemistry, Multidisciplinary
fused-ring systems
ketalization
Marine Toxins - chemical synthesis
Marine Toxins - chemistry
Molecular Structure
natural products
Physical Sciences
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
aldol reaction
fused-ring systems
DOMAIN
STRUCTURAL ELUCIDATION
BIS-SPIROCYCLIZATION
CHEMICAL-SHIFTS
ketalization
HETERO-MICHAEL ADDITION
MYTILUS-EDULIS
natural products
C28-C40 FRAGMENTS
azaspiracids
CONSTRUCTION
PART 1
ABCD
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Summary:Heading south: An efficient approach to the FGHI southern ring system of azaspiracid‐1 is disclosed. Each of the eight stereogenic centers is generated with excellent diastereoselectivity. In addition, the stereochemical outcome of the ketalization steps could be controlled by careful selection of the conditions. Teoc=2‐(trimethylsilyl)ethoxycarbonyl; TMS=trimethylsilyl; TIPS=triisopropylsilyl; Bn=benzyl.
Bibliography:Financial support was provided by the National Institutes of Health (GM63723). The authors would also like to thank Prof. Max Deinzer (OSU) and Dr. Jeff Morré (OSU) for mass spectral data, Rodger Kohnert (OSU) and Dr. Clemens Anklin (Bruker Biospin) for NMR assistance, Damien L. Kupier (OSU) for his synthetic assistance toward aldehyde 18, David J. Weldon (University of Mississippi) for his early work on the synthesis of 32, and Dr. Roger Hanselmann (Rib-X Pharmaceuticals) for helpful discussions.
istex:8FFF0DA8521A2824E861EE4D8230440F08CEA2C1
ark:/67375/WNG-RZ8R5Q20-N
ArticleID:ANIE200603353
National Institutes of Health - No. GM63723
David J. Weldon (University of Mississippi) for his early work on the synthesis of
Financial support was provided by the National Institutes of Health (GM63723). The authors would also like to thank Prof. Max Deinzer (OSU) and Dr. Jeff Morré (OSU) for mass spectral data, Rodger Kohnert (OSU) and Dr. Clemens Anklin (Bruker Biospin) for NMR assistance, Damien L. Kupier (OSU) for his synthetic assistance toward aldehyde
and Dr. Roger Hanselmann (Rib‐X Pharmaceuticals) for helpful discussions.
18
32
Medline
NIH RePORTER
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603353