Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Kyosuke Tanaka, Masahito Watanabe, Kodai Ishibashi, Hiroshi Matsuyama, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

Original languageEnglish
Pages (from-to)1700-1703
Number of pages4
JournalOrganic Letters
Volume12
Issue number8
DOIs
Publication statusPublished - 2010 Apr 16

Fingerprint

quinones
Regioselectivity
Silica Gel
synthesis
Phenol
Skeleton
carbenes
silica gel
Derivatives
musculoskeletal system
Oxidation
phenols
oxidation
quinone methide
kendomycin
benzoquinone
carbene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Tanaka, K., Watanabe, M., Ishibashi, K., Matsuyama, H., Saikawa, Y., & Nakata, M. (2010). Total synthesis of kendomycin featuring intramolecular dötz benzannulation. Organic Letters, 12(8), 1700-1703. https://doi.org/10.1021/ol100229f

Total synthesis of kendomycin featuring intramolecular dötz benzannulation. / Tanaka, Kyosuke; Watanabe, Masahito; Ishibashi, Kodai; Matsuyama, Hiroshi; Saikawa, Yoko; Nakata, Masaya.

In: Organic Letters, Vol. 12, No. 8, 16.04.2010, p. 1700-1703.

Research output: Contribution to journalArticle

Tanaka, K, Watanabe, M, Ishibashi, K, Matsuyama, H, Saikawa, Y & Nakata, M 2010, 'Total synthesis of kendomycin featuring intramolecular dötz benzannulation', Organic Letters, vol. 12, no. 8, pp. 1700-1703. https://doi.org/10.1021/ol100229f
Tanaka K, Watanabe M, Ishibashi K, Matsuyama H, Saikawa Y, Nakata M. Total synthesis of kendomycin featuring intramolecular dötz benzannulation. Organic Letters. 2010 Apr 16;12(8):1700-1703. https://doi.org/10.1021/ol100229f
Tanaka, Kyosuke ; Watanabe, Masahito ; Ishibashi, Kodai ; Matsuyama, Hiroshi ; Saikawa, Yoko ; Nakata, Masaya. / Total synthesis of kendomycin featuring intramolecular dötz benzannulation. In: Organic Letters. 2010 ; Vol. 12, No. 8. pp. 1700-1703.
@article{9386720db6bf4a85b7503c3e45cb7fdf,
title = "Total synthesis of kendomycin featuring intramolecular d{\"o}tz benzannulation",
abstract = "One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular D{\"o}tz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.",
author = "Kyosuke Tanaka and Masahito Watanabe and Kodai Ishibashi and Hiroshi Matsuyama and Yoko Saikawa and Masaya Nakata",
year = "2010",
month = "4",
day = "16",
doi = "10.1021/ol100229f",
language = "English",
volume = "12",
pages = "1700--1703",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Total synthesis of kendomycin featuring intramolecular dötz benzannulation

AU - Tanaka, Kyosuke

AU - Watanabe, Masahito

AU - Ishibashi, Kodai

AU - Matsuyama, Hiroshi

AU - Saikawa, Yoko

AU - Nakata, Masaya

PY - 2010/4/16

Y1 - 2010/4/16

N2 - One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

AB - One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

UR - http://www.scopus.com/inward/record.url?scp=77951156663&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951156663&partnerID=8YFLogxK

U2 - 10.1021/ol100229f

DO - 10.1021/ol100229f

M3 - Article

VL - 12

SP - 1700

EP - 1703

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -