GB1171129A - Improvements in or relating to Ecdysone Steroids - Google Patents

Improvements in or relating to Ecdysone Steroids

Info

Publication number
GB1171129A
GB1171129A GB4953466A GB4953466A GB1171129A GB 1171129 A GB1171129 A GB 1171129A GB 4953466 A GB4953466 A GB 4953466A GB 4953466 A GB4953466 A GB 4953466A GB 1171129 A GB1171129 A GB 1171129A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
compound
give
ecdysone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4953466A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zoecon Corp
Original Assignee
Zoecon Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US506410A external-priority patent/US3378549A/en
Priority claimed from US523019A external-priority patent/US3354154A/en
Priority claimed from US523032A external-priority patent/US3354152A/en
Application filed by Zoecon Corp filed Critical Zoecon Corp
Publication of GB1171129A publication Critical patent/GB1171129A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

1,171,129. Steroids related to ecdysone. ZOECON CORP. 4 Nov., 1966 [4 Nov., 1965; 26 Jan., 1966 (2) ; 26 May, 1966], No. 49534/66. Heading C2U. Compounds of the Formula (I) are prepared by selectively oxidizing compounds of the Formula (II) to give the corresponding 6- ketones, oxidizing the 20-hydroxymethyl group of these by treatment with a dialkylcarbodiimide or dicyoloalkylcarbodiimide and dimethyl sulphoxide in the presence of a strong acid and an organic base to give compounds of the Formula (III), treating these with a lithium derivative of a compound HC#C-YR<SP>2</SP> to give compounds of the Formula (IV) and catalytically hydrogenating these. (in which each of A and B is H or alkyl ; R<SP>1</SP> is H or OH; R<SP>2</SP> is H or tetrahydropyranyloxy; and Y is C 1-6 alkylene or alkylidene). The tetrahydroxypyranyl ether, when present, and the alkylidenedioxy group may then be acid hydrolysed to give ecdysone and related compounds. A 14α-hydroxy group may be introduced in a 14α-H compound by treatment with SeO 2 and a 5α-H compound may be epimerized to the 5#-H compound by treatment with a base. Compounds of the Formula (II) are prepared by reducing an appropriate alkyl 6-keto- 22,23 - bisnorchol - 7 - enoate to the corresponding 6-ol with tri-tert.-butoxide aluminium hydride followed by reduction of the carbalkoxy function with LiAlH 4 .
GB4953466A 1965-11-04 1966-11-04 Improvements in or relating to Ecdysone Steroids Expired GB1171129A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US506410A US3378549A (en) 1965-11-04 1965-11-04 2, 3-acetonides of polyhydroxy bis norchol-7-enoic acid derivatives
US523019A US3354154A (en) 1966-01-26 1966-01-26 2beta, 3beta-alkylidenedioxy-6-hydroxy-22, 23-bisnorchol-7-enoic acid alkyl esters and process for the production thereof
US523032A US3354152A (en) 1966-01-26 1966-01-26 2beta, 3beta-alkylidenedioxy-6-oxygenated-delta-steroids and process for the preparation thereof
US55304166A 1966-05-26 1966-05-26

Publications (1)

Publication Number Publication Date
GB1171129A true GB1171129A (en) 1969-11-19

Family

ID=27504457

Family Applications (3)

Application Number Title Priority Date Filing Date
GB4953266A Expired GB1174082A (en) 1965-11-04 1966-11-04 Improvements concerned with Steroids related to Ecdysone
GB4953466A Expired GB1171129A (en) 1965-11-04 1966-11-04 Improvements in or relating to Ecdysone Steroids
GB4953366A Expired GB1171128A (en) 1965-11-04 1966-11-04 Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB4953266A Expired GB1174082A (en) 1965-11-04 1966-11-04 Improvements concerned with Steroids related to Ecdysone

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB4953366A Expired GB1171128A (en) 1965-11-04 1966-11-04 Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids

Country Status (3)

Country Link
DE (3) DE1593454A1 (en)
FR (1) FR1502168A (en)
GB (3) GB1174082A (en)

Also Published As

Publication number Publication date
GB1174082A (en) 1969-12-10
GB1171128A (en) 1969-11-19
FR1502168A (en) 1967-11-18
DE1593452A1 (en) 1970-07-16
DE1593453A1 (en) 1970-07-16
DE1593454A1 (en) 1971-01-28

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