91444-85-8

Upstream product

• 50-00-0 formaldehyd 
• 61950-54-7 (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 
• 108-98-5 thiophenol 
• 117556-90-8 (8aR)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione 1-ethylene ketal 
• 33878-99-8 (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 100348-93-4 (R)-Wieland-Miescher ketone 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 5073-65-4 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione 

Downstream Products

• 126924-90-1 C₂₁H₂₆O₄S 
• 126924-91-2 C₂₀H₂₄O₄S 
• 126924-92-3 C₂₆H₂₈O₃S₂ 
• 126910-05-2 C₂₈H₃₆O₆ 
• 882-33-7 diphenyldisulfane 
• 126892-18-0 (S)-8a-Methyl-4-methylene-5-phenylsulfanylmethyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 126892-19-1 C₂₀H₂₆O₄S 
• 126892-21-5 C₂₀H₂₂O₄S 
• 126910-03-0 Acetic acid (1R,4aS)-4a-methyl-4,7-dioxo-8-phenylsulfanylmethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ylmethyl ester 
• 126892-20-4 C₂₂H₂₆O₅S 
• 56881-68-6 (+)-pallescensin A 
• 91444-81-4 C₂₁H₂₈O₃ 

Relevant academic research and scientific papers

Nodulisporic acid A synthetic studies. 2. Construction of an eastern hemisphere subtarget.

In this, the second of two Letters, we describe an effective assembly of (+)-4, an eastern hemisphere subtarget comprising the FGH rings of (+)-nodulisporic acid A (1) (17 steps, 9% overall yield). Central to the synthesis is a Koga three-component conjug

Synthesis of the ABC skeleton of the aglycon of Echinoside A

Echinoside A is a triterpene saponin isolated from the sea cucumber Actinopyga echinites (JAEGER), which displays potent antitumor activities in vitro and in vivo. Here, we report the synthesis of the ABC-fused ring skeleton of the aglycon of Echinoside A, with the enantiomerically pure (+)-Wieland-Miescher ketone being used as starting material and a Robinson annulation as the key reaction.

Development of a scalable synthesis of a common eastern tricyclic lactone for construction of the nodulisporic acids

A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+

Synthesis of manool-related labdane diterpenes as platelet aggregation inhibitors

Enantioselective total synthesis of the labdane diterpene (-)-1, was achieved starting from the R-(-)-enantiomer of the Wieland-Miescher ketone (3). The enantiomer (+)-1 was obtained by partial synthesis via microbial transformation of sclareol (24). These results established that the natural compound (+)-1, a platelet aggregation inhibitor, has a normal absolute stereochemistry like that of manool (2). The B-norlabdane-related compound 44 was also synthesized using a novel ring contraction reaction.

Regio- and stereoselective functionalizations of the Wieland-Miescher ketone derivatives at the C-8 position

New efficient methods for stereoselective hydroxymethylation, hydroxylation, and thiophenylation at the C-8 position of the Wieland-Miescher ketone derivatives (2-4) have been developed by diverse modifications from the Kirk-Petrow reaction, which involve autoxidation for the hydroxylation.Keywords - Wieland-Miescher ketone; Kirk-Petrow reaction; phenylthio-methylation; hydroxylation; hydroxymethylation; thiophenylation.

Indole Diterpene Synthetic Studies. 2. First-Generation Total Synthesis of (-)-Paspaline

We record here a full account of the first total synthesis of (-)-paspaline (1), the simplest member of a rapidly growing class of architecturally complex diterpene indole alkaloids, many of which possess potent tremorgenic activity.In terms of sequential annulation, the strategy involves the following operations: DE -> CDE -> CDEF -> ABCDEF.Proceeding in 23 steps from Wieland-Miescher ketone, the synthesis afforded (-)-paspaline (1) in high enantiomeric purity.

An Efficient Approach to Chiral, Nonracemic trans-Decahydro-5,8a-dimethyl-1,6-naphthalenedione Derivatives: Total Synthesis of (+)-Pallescensin A

The syntheses of of six chiral, nonracemic trans-decahydro-5,8a-dimethyl-1,6-naphthalenedione derivatives 1a-f are described.The approach calls for the reductive alkylation of enone 4 readily available from (+)-Wieland-Miescher ketone (5) via chemoselective ketalization on the C(8)-carbonyl followed by application of the Kirk-Petrow (phenylthio)methylation protocol.Yields for reactive electrophiles are in the range of 70-85percent.To demonstrate the utility of this method, we record here a nine-step total synthesis of (+)-pallescensin A (8); the overall yield from enone 4 was 13percent.