Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries

Kiyoto Sawamura, Keigo Yoshida, Akari Suzuki, Toru Motozaki, Ikuko Kozawa, Takashi Hayamizu, Ryosuke Munakata, Kenichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

(Chemical Equation Presented) Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.

Original languageEnglish
Pages (from-to)6143-6148
Number of pages6
JournalJournal of Organic Chemistry
Volume72
Issue number16
DOIs
Publication statusPublished - 2007 Aug

Fingerprint

Stereochemistry
Macrolides
tubelactomicin B
tubelactomicin D

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Sawamura, K., Yoshida, K., Suzuki, A., Motozaki, T., Kozawa, I., Hayamizu, T., ... Tadano, K. I. (2007). Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries. Journal of Organic Chemistry, 72(16), 6143-6148. https://doi.org/10.1021/jo0708442

Total syntheses of natural tubelactomicins B, D, and E : Establishment of their stereochemistries. / Sawamura, Kiyoto; Yoshida, Keigo; Suzuki, Akari; Motozaki, Toru; Kozawa, Ikuko; Hayamizu, Takashi; Munakata, Ryosuke; Takao, Kenichi; Tadano, Kin Ichi.

In: Journal of Organic Chemistry, Vol. 72, No. 16, 08.2007, p. 6143-6148.

Research output: Contribution to journalArticle

Sawamura, K, Yoshida, K, Suzuki, A, Motozaki, T, Kozawa, I, Hayamizu, T, Munakata, R, Takao, K & Tadano, KI 2007, 'Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries', Journal of Organic Chemistry, vol. 72, no. 16, pp. 6143-6148. https://doi.org/10.1021/jo0708442
Sawamura, Kiyoto ; Yoshida, Keigo ; Suzuki, Akari ; Motozaki, Toru ; Kozawa, Ikuko ; Hayamizu, Takashi ; Munakata, Ryosuke ; Takao, Kenichi ; Tadano, Kin Ichi. / Total syntheses of natural tubelactomicins B, D, and E : Establishment of their stereochemistries. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 16. pp. 6143-6148.
@article{0ff9de9588464bbf8640dbfc1879315c,
title = "Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries",
abstract = "(Chemical Equation Presented) Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.",
author = "Kiyoto Sawamura and Keigo Yoshida and Akari Suzuki and Toru Motozaki and Ikuko Kozawa and Takashi Hayamizu and Ryosuke Munakata and Kenichi Takao and Tadano, {Kin Ichi}",
year = "2007",
month = "8",
doi = "10.1021/jo0708442",
language = "English",
volume = "72",
pages = "6143--6148",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Total syntheses of natural tubelactomicins B, D, and E

T2 - Establishment of their stereochemistries

AU - Sawamura, Kiyoto

AU - Yoshida, Keigo

AU - Suzuki, Akari

AU - Motozaki, Toru

AU - Kozawa, Ikuko

AU - Hayamizu, Takashi

AU - Munakata, Ryosuke

AU - Takao, Kenichi

AU - Tadano, Kin Ichi

PY - 2007/8

Y1 - 2007/8

N2 - (Chemical Equation Presented) Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.

AB - (Chemical Equation Presented) Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.

UR - http://www.scopus.com/inward/record.url?scp=34547619044&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547619044&partnerID=8YFLogxK

U2 - 10.1021/jo0708442

DO - 10.1021/jo0708442

M3 - Article

C2 - 17625888

AN - SCOPUS:34547619044

VL - 72

SP - 6143

EP - 6148

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 16

ER -