Total Synthesis of Altohyrtin A (Spongistatin 1): Part 2

Hayward, Matthew M.; Roth, Rebecca M.; Duffy, Kevin J.; Dalko, Peter I.; Stevens, Kirk L.; Guo, Ji-Ming; Kishi, Yoshito

doi:10.1002/(sici)1521-3773(19980202)37:1/2<190::aid-anie190>3.3.co;2-s

Cited by 31 publications

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“…These studies would identify in which order the remaining EFGHI-region of the molecule should be assembled. One possible option we investigated as a viable C20–C21 fragment coupling was a chelate-controlled vinyllithium addition 65,66 to a D-ring aldehyde synthon 65 (eq 8). As facile elaboration of the C21-1,1-disubstituted olefin was thought to be incompatible with the two olefins contained in the AB-ring fragment 7 , this C20–C21 bond construction to join the CD- and the E-ring fragments was investigated prior to the introduction of the AB-ring fragment.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis

et al. 2008

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The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the non-acyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis

et al. 2008

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“…Subjection of this mixture to Zn powder in THF/NH 4 OAc induced deprotection31 of the trichloroethyl (TCE) ester to give the seco ‐acid 35 . Regioselective macrolactonization6c, 7b, 8b, 32 of the triol 35 , which engaged the C41 hydroxy group (in preference to those at C42 and C38), was performed under modified Yamaguchi conditions33 to produce the 42‐membered macrolide 36 in 55 % yield. Finally, exposure to HF/MeCN led to deprotection of the four silyl ethers and hydrolysis of the remaining methyl acetal to provide (+)‐altohyrtin A/spongistatin 1 ( 1 ) in 36 % yield 34.…”

Section: Methodsmentioning

confidence: 99%

Stereocontrolled Total Synthesis of (+)-Altohyrtin A/Spongistatin 1 Financial support was provided by the EPSRC (GR/L41646), Cambridge Commonwealth Trust (Scholarship to M.J.C.), EC (Marie Curie Postdoctoral Fellowship to J.L.A.), DFG (Postdoctoral Fellowship to T.T.), NSERC-Canada (Postdoctoral Fellowship to R.M.O.), Churchill College (Research Fellowship to D.J.W.), Kingapos;s College and Sims Fund, Cambridge (Scholarship to D.Y.K.C.). We also thank Merck and AstraZeneca Pharmaceuticals for generous supp

Paterson

Chen

Coster

et al. 2001

Angew. Chem. Int. Ed.

115

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As an exceptionally potent antimitotic macrolide, altohyrtin A/spongistatin 1 shows great promise in cancer chemotherapy but its extreme scarcity in the natural sponges has halted its further preclinical development. A highly stereocontrolled total synthesis, which exploits boron‐mediated aldol bond constructions, has been realized to provide, for the first time, a useful amount of synthetic material.

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“…The proposed configuration for spongistatin 1 263 [ 96 , 99 ] was in disagreement with the proposed configuration of the other compounds [ 98 , 100 ]. The absolute configurations of spongistatin 1 263 here depicted were only determined by synthesis in subsequent studies by other authors [ 101 , 102 ]. The authors suggest that the depicted configurations are common to all the members of this class of spongipyran natural products.…”

Section: Macrolidesmentioning

confidence: 99%

The Role of Spongia sp. in the Discovery of Marine Lead Compounds

et al. 2016

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A comprehensive review on the chemistry of Spongia sp. is here presented, together with the biological activity of the isolated compounds. The compounds are grouped in sesquiterpene quinones, diterpenes, C21 and other linear furanoterpenes, sesterterpenes, sterols (including secosterols), macrolides and miscellaneous compounds. Among other reports we include studies on the intraspecific diversity of a Mediterranean species, compounds isolated from associated sponge and nudibranch and compounds isolated from S. zimocca and the red seaweed Laurentia microcladia. Under biological activity a table of the reported biological activities of the various compounds and the biological screening of extracts are described. The present review covers the literature from 1971 to 2015.

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Total Synthesis of Altohyrtin A (Spongistatin 1): Part 2

Cited by 31 publications

References 0 publications

Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis

Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis

The Role of Spongia sp. in the Discovery of Marine Lead Compounds

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