A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

Hugo Lago-Santomé; Rubén Meana-Pañeda; Ricardo Alonso

doi:10.1021/jo500056w

A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

Hugo Lago-Santomé
, Rubén Meana-Pañeda
, Ricardo Alonso

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3- dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.

Original language	English (US)
Pages (from-to)	4300-4305
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	79
Issue number	10
DOIs	https://doi.org/10.1021/jo500056w
State	Published - May 16 2014

Publisher link

10.1021/jo500056w

Find It

Find It at U of M Libraries

Cite this

@article{e72b23b5f7d544ab867db7c1d1762e66,

title = "A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin",

abstract = "A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3- dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.",

author = "Hugo Lago-Santom{\'e} and Rub{\'e}n Meana-Pa{\~n}eda and Ricardo Alonso",

year = "2014",

month = may,

day = "16",

doi = "10.1021/jo500056w",

language = "English (US)",

volume = "79",

pages = "4300--4305",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

AU - Lago-Santomé, Hugo

AU - Meana-Pañeda, Rubén

AU - Alonso, Ricardo

PY - 2014/5/16

Y1 - 2014/5/16

N2 - A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3- dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.

AB - A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3- dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.

UR - https://www.scopus.com/pages/publications/84900849040

UR - https://www.scopus.com/pages/publications/84900849040#tab=citedBy

U2 - 10.1021/jo500056w

DO - 10.1021/jo500056w

M3 - Article

C2 - 24735167

AN - SCOPUS:84900849040

SN - 0022-3263

VL - 79

SP - 4300

EP - 4305

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this