Journal article
Towards the synthesis of massadine: a unified strategy for the stereoselective synthesis of the carbocyclic C,D-ring subunit.
- Breder A ETH Zürich HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland.
- Chinigo GM
- Waltman AW
- Carreira EM
- 2011-09-21
Published in:
- Chemistry (Weinheim an der Bergstrasse, Germany). - 2011
English
Massadine is a hexacyclic marine natural product, which belongs to the family of pyrrole-imidazole alkaloids. Herein, we describe a unified approach to the C,D-ring subunit of this sponge metabolite based on the exploitation of a norbornene scaffold for the stereocontrolled construction of massadine's carbon skeleton. Highlights of the sequence presented include the application of a stereospecific norbornyl rearrangement for facile introduction of an oxygen at the C7-position within the norbornene nucleus, a highly regioselective and end group differentiating ozonolytic scission of a C-C double bond, and an oxidative decarboxylation reaction for the installation of the hindered secondary C2-alcohol function. Furthermore, the iterative assembly of the two guanidine entities as well as the implementation of the spirocyclic junction between the C- and the D-rings are described. Collectively, these key transformations permit an entry to an appropriately functionalized carbon framework, which will serve as a starting point for our efforts toward the completion of the synthesis of massadine.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1002/chem.201101862
- PMID 21932242
- Persistent URL
- https://sonar.ch/global/documents/167893
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