Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-one

Seiichiro Ogawa; Yoshikazu Iwasawa; Taisuke Nose; Tetsuo Suami; Shigeru Ohba; Masatoki Ito; Yoshihiko Saito

doi:10.1039/P19850000903

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-one

Seiichiro Ogawa, Yoshikazu Iwasawa, Taisuke Nose, Tetsuo Suami, Shigeru Ohba, Masatoki Ito and Yoshihiko Saito

Abstract

The optical resolution of (±)-7-endo-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid (±)-(1) has been accomplished by use of (R)-(+)- and (S)-(–)-α-methylbenzylamine, respectively. The absolute configuration of (–)-(1) has been determined on the basis of X-ray analysis of the bromo lactone (2) derived from it. The title branched-chain cyclitol (6), the antibiotic produced by Streptomyces sp. MA-4145, has been totally synthesized from (–)-(1), its absolute configuration being established. Synthesis of the penta-N,O-acetyl derivative (12) of (+)-validamine, the branched-chain aminocyclitol obtained by degradation of the antibiotic validamycin A, has also been carried out from (–)-(1).

Download options Please wait...

Article information

DOI: https://doi.org/10.1039/P19850000903
Article type: Paper

Download Citation

J. Chem. Soc., Perkin Trans. 1, 1985, 903-906

Permissions

Request permissions

Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-one

S. Ogawa, Y. Iwasawa, T. Nose, T. Suami, S. Ohba, M. Ito and Y. Saito, J. Chem. Soc., Perkin Trans. 1, 1985, 903 DOI: 10.1039/P19850000903

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Fetching data from CrossRef.
This may take some time to load.

Journal of the Chemical Society, Perkin Transactions 1

Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-one

Abstract

Article information

Download Citation

Permissions

Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-one

Search articles by author

Spotlight

Advertisements