Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment

M C  Clasby; D  Craig; A A  JaxaChamiec; J Y Q  Lai; A  Marsh; A M Z  Slawin; A J P  White; D J  Williams

Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment

M C Clasby, D Craig, A A JaxaChamiec, J Y Q Lai, A Marsh, A M Z Slawin, A J P White, D J Williams

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Abstract

The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D-3 synthesis.

Original language	English
Pages (from-to)	4769-4802
Number of pages	34
Journal	Tetrahedron
Volume	52
Issue number	13
Publication status	Published - 25 Mar 1996

Keywords

STEREOCONTROLLED SYNTHESIS
STEREOSELECTIVE SYNTHESIS
GRUNDMANN KETONE
SYSTEM

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title = "Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment",

abstract = "The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D-3 synthesis.",

keywords = "STEREOCONTROLLED SYNTHESIS, STEREOSELECTIVE SYNTHESIS, GRUNDMANN KETONE, SYSTEM",

author = "Clasby, \{M C\} and D Craig and JaxaChamiec, \{A A\} and Lai, \{J Y Q\} and A Marsh and Slawin, \{A M Z\} and White, \{A J P\} and Williams, \{D J\}",

year = "1996",

month = mar,

day = "25",

language = "English",

volume = "52",

pages = "4769--4802",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "13",

}

TY - JOUR

T1 - Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment

AU - Clasby, M C

AU - Craig, D

AU - JaxaChamiec, A A

AU - Lai, J Y Q

AU - Marsh, A

AU - Slawin, A M Z

AU - White, A J P

AU - Williams, D J

PY - 1996/3/25

Y1 - 1996/3/25

N2 - The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D-3 synthesis.

AB - The enantiospecific synthesis of the vitamin D-3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D-3 synthesis.

KW - STEREOCONTROLLED SYNTHESIS

KW - STEREOSELECTIVE SYNTHESIS

KW - GRUNDMANN KETONE

KW - SYSTEM

UR - https://www.scopus.com/pages/publications/0029975069

M3 - Article

SN - 0040-4020

VL - 52

SP - 4769

EP - 4802

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

Vitamin D-3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment

Abstract

Keywords

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