Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation

Satoshi Adachi; Kana Watanabe; Yusuke Iwata; Shunsuke Kameda; Yoshihito Miyaoka; Masao Onozuka; Ryo Mitsui; Yoko Saikawa; Masaya Nakata

doi:10.1002/anie.201209205

Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation

Satoshi Adachi, Kana Watanabe, Yusuke Iwata, Shunsuke Kameda, Yoshihito Miyaoka, Masao Onozuka, Ryo Mitsui, Yoko Saikawa, Masaya Nakata

Department of Applied Chemistry

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

38 Citations (Scopus)

Abstract

The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler-Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.

Original language	English
Pages (from-to)	2087-2091
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	7
DOIs	https://doi.org/10.1002/anie.201209205
Publication status	Published - 2013 Feb 11

Keywords

Bischler-Napieralski cyclization
glycosylation
natural products
polyketides
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201209205

Cite this

@article{0854c21b7ac9465d9c69dfad688d95aa,

title = "Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation",

abstract = "The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler-Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.",

keywords = "Bischler-Napieralski cyclization, glycosylation, natural products, polyketides, total synthesis",

author = "Satoshi Adachi and Kana Watanabe and Yusuke Iwata and Shunsuke Kameda and Yoshihito Miyaoka and Masao Onozuka and Ryo Mitsui and Yoko Saikawa and Masaya Nakata",

year = "2013",

month = feb,

day = "11",

doi = "10.1002/anie.201209205",

language = "English",

volume = "52",

pages = "2087--2091",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "7",

}

TY - JOUR

T1 - Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation

AU - Adachi, Satoshi

AU - Watanabe, Kana

AU - Iwata, Yusuke

AU - Kameda, Shunsuke

AU - Miyaoka, Yoshihito

AU - Onozuka, Masao

AU - Mitsui, Ryo

AU - Saikawa, Yoko

AU - Nakata, Masaya

PY - 2013/2/11

Y1 - 2013/2/11

N2 - The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler-Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.

AB - The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler-Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.

KW - Bischler-Napieralski cyclization

KW - glycosylation

KW - natural products

KW - polyketides

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84873541676&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84873541676&partnerID=8YFLogxK

U2 - 10.1002/anie.201209205

DO - 10.1002/anie.201209205

M3 - Article

C2 - 23303690

AN - SCOPUS:84873541676

SN - 1433-7851

VL - 52

SP - 2087

EP - 2091

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Total syntheses of lactonamycin and lactonamycin Z with late-stage a-ring formation and glycosylation

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this