Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

Toshimi Anzo; Akari Suzuki; Kiyoto Sawamura; Toru Motozaki; Madoka Hatta; Ken ichi Takao; Kin ichi Tadano

doi:10.1016/j.tetlet.2007.10.002

Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

Toshimi Anzo, Akari Suzuki, Kiyoto Sawamura, Toru Motozaki, Madoka Hatta, Ken ichi Takao, Kin ichi Tadano

Department of Applied Chemistry

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

15 Citations (Scopus)

Abstract

A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.

Original language	English
Pages (from-to)	8442-8448
Number of pages	7
Journal	Tetrahedron Letters
Volume	48
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2007.10.002
Publication status	Published - 2007 Nov 26

Keywords

Hiyama coupling
Macrolide antibiotics
Ring-closing olefin metathesis
Transannular Diels-Alder reaction
Tubelactomicins

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2007.10.002

Cite this

@article{a07bb96a3af64e54890afbb976e6f30e,

title = "Formal synthesis of tubelactomicins via a transannular Diels-Alder approach",

abstract = "A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.",

keywords = "Hiyama coupling, Macrolide antibiotics, Ring-closing olefin metathesis, Transannular Diels-Alder reaction, Tubelactomicins",

author = "Toshimi Anzo and Akari Suzuki and Kiyoto Sawamura and Toru Motozaki and Madoka Hatta and Takao, {Ken ichi} and Tadano, {Kin ichi}",

year = "2007",

month = nov,

day = "26",

doi = "10.1016/j.tetlet.2007.10.002",

language = "English",

volume = "48",

pages = "8442--8448",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "48",

}

TY - JOUR

T1 - Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

AU - Anzo, Toshimi

AU - Suzuki, Akari

AU - Sawamura, Kiyoto

AU - Motozaki, Toru

AU - Hatta, Madoka

AU - Takao, Ken ichi

AU - Tadano, Kin ichi

PY - 2007/11/26

Y1 - 2007/11/26

N2 - A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.

AB - A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.

KW - Hiyama coupling

KW - Macrolide antibiotics

KW - Ring-closing olefin metathesis

KW - Transannular Diels-Alder reaction

KW - Tubelactomicins

UR - http://www.scopus.com/inward/record.url?scp=35548977936&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35548977936&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2007.10.002

DO - 10.1016/j.tetlet.2007.10.002

M3 - Article

AN - SCOPUS:35548977936

SN - 0040-4039

VL - 48

SP - 8442

EP - 8448

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this