Journal article

A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline.

Abstract:: [reaction: see text] A flexible route to polyhydroxylated pyrrolizidine alkaloids is described, starting from commercially available N-Boc pyrrole and using a partial reduction as the key step. Tactics for varying the stereochemistry around the ring by choice of partial reduction conditions are discussed and methods for constructing the bicyclic ring system of the pyrrolizidine targets are examined. Intramolecular S(N)2 type displacement reactions were found to be an efficient way of forming ...
Expand abstract
Collapse abstract

Publication status:: Published

Actions

Email

Email this record

Send the bibliographic details of this record to your email address.

Your Email
Please enter the email address that the record information will be sent to.

-
Your message (optional)
Please add any additional information to be included within the email.
Cite

Cite this record

APA Style

Donohoe, T., Sintim, H., & Hollinshead, J. (2005). A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline. Journal of Organic Chemistry, 70(18), 7297–7304.

MLA Style

Donohoe, T., et al. “A Noncarbohydrate Based Approach to Polyhydroxylated Pyrrolidizines: Total Syntheses of the Natural Products Hyacinthacine A1 and 1-Epiaustraline.” Journal of Organic Chemistry, vol. 70, no. 18, 2005, pp. 7297–304.

Chicago Style

Donohoe, T, H Sintim, and J Hollinshead. 2005. “A Noncarbohydrate Based Approach to Polyhydroxylated Pyrrolidizines: Total Syntheses of the Natural Products Hyacinthacine A1 and 1-Epiaustraline.” Journal of Organic Chemistry 70 (18): 7297–7304.
Tweet
Print

Access Document

Publisher copy:: 10.1021/jo050977s

Authors

+ Donohoe, T More by this author

Institution:

University of Oxford

Division:

MPLS

Department:

Chemistry

Sub department:

Organic Chemistry

Role:

Author

+ Sintim, H More by this author

Role:

Author

+ Hollinshead, J More by this author

Role:

Author

Bibliographic Details

Journal:: Journal of organic chemistry More from this journal
Volume:: 70
Issue:: 18
Pages:: 7297-7304
Publication date:: 2005-09-01
DOI:: 10.1021/jo050977s
EISSN:: 1520-6904
ISSN:: 0022-3263

Item Description

Language:: English
Keywords:: Stereoisomerism

Pyrroles

Pyrrolizidine Alkaloids

Molecular Conformation

Magnetic Resonance Spectroscopy
Pubs id:: pubs:39662
UUID:: uuid:5e0b784a-2ffd-48ef-a004-430cc77d8e68
Local pid:: pubs:39662
Source identifiers:: 39662
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2005

Licence:: Terms and Conditions of Use for Oxford University Research Archive

Metrics

Views and Downloads

About views and downloads

If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP