201354-99-6

Upstream product

• 638222-34-1 (2R,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-2-(2-ethylprop-2-en-1-yl)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecane 
• 87841-68-7 (4R)-4-(Benzyloxy)pentan-2-one 
• 862475-35-2 (R)-5-(p-methoxybenzyloxy)-4-(triethylsiloxy)-1-pentene 
• 862475-37-4 (2RS,4R)-5-(p-methoxybenzyloxy)-4-(triethylsiloxy)-pentane-1,2-diol 
• 201355-04-6 (2R,4S,6R,8R,10S)-8-Allyl-10-methoxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 201355-06-8 (4R,6R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-oct-1-en-4-ol 
• 201355-05-7 (3R)-3-methoxy-5-(tert-butyldimethylsilyloxy)-pentanal 
• 862475-32-9 (3S)-1-(tert-butyldimethylsilyloxy)-3-methoxy-hex-5-ene 
• 194342-84-2 (R)-1-[(4-methoxybenzyl)oxy]pent-4-en-2-ol 
• 127793-65-1 (3S)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol 
• 121289-23-4 p-methoxybenzyloxyacetaldehyde 
• 445423-03-0 C₃₂H₄₉BO₂ 
• 445423-09-6 (2R,4S,6R,8R,10S)-8-(2-ethylallyl)-10-methoxy-2-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undecan-4-ol 

Downstream Products

• 218799-02-1 C₅₇H₉₃Cl₃O₁₅Si₂ 
• 639087-36-8 C₄₁H₆₉BO₇Si 
• 639087-37-9 C₅₈H₉₆O₁₅Si₂ 
• 218799-03-2 C₅₉H₉₅Cl₃O₁₆Si₂ 

Relevant academic research and scientific papers

Total synthesis of Spongistatin 1: A synthetic strategy exploiting its latent pseudo-symmetry

(Chemical Equation Presented) The challenging structure and potent growth inhibition properties against a variety of human cancer cell lines make Spongistatin 1 (1) an exciting target for total synthesis. Enantioselective total synthesis has been achieved

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The CD-spiroacetal segment

Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.

A Practical and Efficient Synthesis of the C-16-C-28 Spiroketal Fragment (CD) of the Spongistatins

(Equation Presented) A practical and efficient route to the CD spiroketal (C-16-C-28) of the spongistatins is reported. Two stereocenters are introduced from chiral building blocks with the remainder introduced by substrate-controlled transformations. The

Total synthesis of altohyrtin A (spongistatin 1): An alternative synthesis of the CD-spiroacetal subunit

The CD-spiroacetal containing C16-C28 subunit 2, as used in the total synthesis of the potent cytotoxic macrolide, altohyrtin A (spongistatin 1), was prepared by an alternative route using substrate-based stereocontrol in the two ald

Studies in marine macrolide synthesis: Synthesis of a C16-C28 subunit of spongistatin 1 (altohyrtin A) incorporating the CD-spisoacetal moiety

The C16-C28 ketone 3, containing the CD-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from aldehyde 9. Both thermodynamic and kinetic conditions were explored for controlling the CD-acetal configuration.