82225-47-6

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InChI:InChI=1/C23H34O6/c1-14-11-19(29-15(2)24)23(4)17(21(26)27-5)7-6-8-18(23)22(14,3)10-9-16-12-20(25)28-13-16/h12,14,17-19H,6-11,13H2,1-5H3/t14-,17+,18-,19+,22-,23+/m1/s1

Upstream product

• 73818-55-0 Bestmann ylide 
• 82528-09-4 (1R,4aR,5S,6R,8S,8aR)-8-Acetoxy-5-(4-hydroxy-3-oxo-butyl)-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 82527-98-8 (1R,4aR,5S,6R,8S,8aR)-5-(2-Methoxycarbonyl-ethyl)-8-methoxymethoxy-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 82528-00-5 (1R,4aR,5S,6R,8S,8aR)-5-(2-Carboxy-ethyl)-8-methoxymethoxy-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid 
• 82528-00-5 (4aR,5S,6R,8S,8aR)-5-(2-Carboxy-ethyl)-8-methoxymethoxy-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid 
• 82527-94-4 3-((1S,2R,4S,4aR,5R,8aR)-5-Hydroxymethyl-4-methoxymethoxy-1,2,4a-trimethyl-decahydro-naphthalen-1-yl)-propan-1-ol 
• 82527-94-4 3-((1S,2R,4S,4aR,8aR)-5-Hydroxymethyl-4-methoxymethoxy-1,2,4a-trimethyl-decahydro-naphthalen-1-yl)-propan-1-ol 
• 82527-93-3 (1S,3R,4S,4aR,8aR)-4-Allyl-3,4,8a-trimethyl-8-methylene-decahydro-naphthalen-1-ol 
• 82528-04-9 (1R,4aR,5S,6R,8S,8aR)-8-Acetoxy-5-(2-carboxy-ethyl)-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 82528-02-7 (1R,4aR,5S,6R,8S,8aR)-5-(2-Carboxy-ethyl)-8-methoxymethoxy-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 82527-95-5 3-((1S,2R,4S,4aR,5R,8aR)-5-Formyl-4-methoxymethoxy-1,2,4a-trimethyl-decahydro-naphthalen-1-yl)-propionic acid 
• 82528-03-8 (1S,4aS,5R,6S,8R,8aS)-5-(2-Carboxy-ethyl)-8-hydroxy-5,6,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 82527-96-6 ((1S,4aS,8aR)-1-Allyl-1,4a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yloxy)-trimethyl-silane 
• 82538-03-2 (1S,2R,4S,4aR,8aR)-1-Allyl-4-methoxymethoxy-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene 

Relevant academic research and scientific papers

NEO-CLERODANE DITERPENES FROM AJUGA CILIATA VAR. VILLOSIOR

From the aerial parts of Ajuga ciliata var. villosior, nine new neo-clerodane diterpenes have been isolated.The structures of two acetyl derivatives of (12S)-6α, 12,19-trihydroxy-1β--4,18-epoxyneo-clerod-13(14)-en-15,16-olide, three acetyl derivatives of (12S)-1β,6α,19-trihydroxy-12--4,18-epoxyneo-clerod-13(14)-en-15,16-olide, three acetyl derivatives of (12S)-6α,19-dihydroxy-12--4,18-epoxyneo-clerod-13(14)-en-15,16-olide and methyl 6α-hydroxy-4α-methoxycarbonyl-18-norneo-clerod-13(14)-en-15,16-olide were elucidated by spectroscopic methods and chemical correlation.In addition, a known neo-clerodane, ajugarin-IV, was isolated.Keywords: neo-clerodane; Ajuga ciliata var. villosior; bitter principle; diterpene; Labiatae; ajugamarin

STEREOSPECIFIC TOTAL SYNTHESIS OF AJUGARIN-IV

A stereospecific sequence from the octalindione 2 leads in 21 steps to the new insecticide ajugarin-IV.Formation of the butenolide portion is conveniently achieved from acid 21 by sucessive use of the reagents tris(trimethylsiloxy)ethylene and ketenylidenetriphenylphosphorane.