Synthesis of (+)-Obtusenyne

S Y Frankie Mak; Neil R Curtis; Andrew N Payne; Miles S Congreve; Andrew J Wildsmith; Craig L Francis; John E Davies; Sofia I Pascu; Jonathan W Burton; Andrew B Holmes

doi:10.1002/chem.200701567

Synthesis of (+)-Obtusenyne

S Y Frankie Mak, Neil R Curtis, Andrew N Payne, Miles S Congreve, Andrew J Wildsmith, Craig L Francis, John E Davies, Sofia I Pascu, Jonathan W Burton, Andrew B Holmes

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

27 Citations (SciVal)

Abstract

An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

Original language	English
Pages (from-to)	2867-2885
Number of pages	19
Journal	Chemistry - A European Journal
Volume	14
Issue number	9
DOIs	https://doi.org/10.1002/chem.200701567
Publication status	Published - 17 Mar 2008

Access to Document

10.1002/chem.200701567

Cite this

@article{effaaf081ac147c7972a01a05219bdfe,

title = "Synthesis of (+)-Obtusenyne",

abstract = "An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.",

author = "Mak, \{S Y Frankie\} and Curtis, \{Neil R\} and Payne, \{Andrew N\} and Congreve, \{Miles S\} and Wildsmith, \{Andrew J\} and Francis, \{Craig L\} and Davies, \{John E\} and Pascu, \{Sofia I\} and Burton, \{Jonathan W\} and Holmes, \{Andrew B\}",

year = "2008",

month = mar,

day = "17",

doi = "10.1002/chem.200701567",

language = "English",

volume = "14",

pages = "2867--2885",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc.",

number = "9",

}

TY - JOUR

T1 - Synthesis of (+)-Obtusenyne

AU - Mak, S Y Frankie

AU - Curtis, Neil R

AU - Payne, Andrew N

AU - Congreve, Miles S

AU - Wildsmith, Andrew J

AU - Francis, Craig L

AU - Davies, John E

AU - Pascu, Sofia I

AU - Burton, Jonathan W

AU - Holmes, Andrew B

PY - 2008/3/17

Y1 - 2008/3/17

N2 - An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

AB - An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

UR - https://www.scopus.com/pages/publications/53849140858

UR - http://dx.doi.org/10.1002/chem.200701567

U2 - 10.1002/chem.200701567

DO - 10.1002/chem.200701567

M3 - Article

SN - 0947-6539

VL - 14

SP - 2867

EP - 2885

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 9

ER -

Synthesis of (+)-Obtusenyne

Abstract

Access to Document

Other files and links

Fingerprint

Cite this